Zur Konstitution des Kantharidins. Eine eigenartige Zerfallsreaktion des Kantharidins

Bruchhausen, F. V.; Bersch, H. W.

doi:10.1002/ardp.192800187

Cited by 28 publications

(9 citation statements)

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“…5 mg (0,552 mmol) (61, 202 (loo), 111 (13), 109 (5). 93 (7), 91 (8), 77 (16), 67 (€9, 65 (5), 55 (17), 54 (8), 53 (12), 51 (6). 44 (S), 43 (16).…”

Section: Acetoxy-cyclohex-l(mentioning

confidence: 99%

“…36,9 mg (0,196 mrnol) 90 ( m ; H-(4)), 4,15 ( m ; H,-(10) und Hz-(ll)), 2,03 und 2,OO (zwei s ; Intensitatsverhaltnis ca. 2 : 1 ; drei CH3CO), 1,2 ( m ;, H,- (5) und H,-(G)), 1,02 und 1,OO (zwei s ; H3- (8) und H3-(9)). -MS.: 314 (M+, nil), 152 (12), 139 (15).…”

Section: (-)-2a3a-dimethyl-perhydroisobenzofuran-4/3-ol ((-)-11)11)unclassified

“…unter (24), 140 (12), 137 (15), 125 (5), 123 (23), 122 (21), 121 (lo), 111 (12), 110 ( Z O ) , 109 (loo), 108 (15), 107 (21), 98 (9), 97 (32), 96 (30), 95 (31), 94 (131, 93 (18), 91 (9), 85 (5), 84 (20), 83 (19), 82 (251, 81 (42), 80 (5), 79 (15). 77 (lo), 71 (13), 70 (27), 69 (31), 68 ( l l ) , 67 (35), 65 (7), 57 (23), 56 (8), 55 (50), 54 (7), Hz-(l), H,-(5) und H2- (6)), 0,99 und 0,96 (zwei s ; H3- (8) und H,- (9)). H3-(9)).…”

Section: (-)-2a3a-dimethyl-perhydroisobenzofuran-4/3-ol ((-)-11)11)unclassified

“…-MS.: 319 (Mf. nil), 153 (12), 152 (loo), 151 (17), 150 (65), 139 (5), 138 (5), 137 (41), 135 (11), 124 (7), 123 (22), 122 (33), 121 (27), 120 (21), 111 (12), 110 (38), 109 (75), 108 (22), 107 (50), 106 (13), 105 (11), 104 (52), 97 (21), 96 (lo), 95 (37), 94 ( 2 6 ) , 93 (37), 92 (24), 91 (15), 84 (30)' 83 ( l l ) , 82 (18), 81 (33), 80 (8), 79 (22), 77 (18), 76 (45), 75 (16), 74 (7), 53 (25), 51 (8), 45 (5), 44 (16), 43 (58), 42 (11), 41 (84). 190 mg (-)-12 wurden wie in 3.1.4 beschrieben in 15 ml Methanol und 0,25 ml 2~ Natriummethylat-Losung in Methanol umgesetzt und aufgearbeitet.…”

Section: (-)-2a3a-dimethyl-perhydroisobenzofuran-4/3-ol ((-)-11)11)unclassified

“…Rei der Chromatographie an 20 g Kieselgel wurde der p-Nitrobenzocsaure-methylester rnit Ather /Hexan 1 : 1, und das ( -)- (2 S, 3R, 4R)-2,3-DimethyZ-perhydroisobe~zzofuran-4-oZ (( -)-11) ( 3-)-2a, 3a-DirnethyZ-4P-hydro~y-(A~(~))-tetrahydrophthalid (( -+)-17)13). (12), 96 (5), 95 (17), 94 (7), 93 (Il), 92 ( 5 ) , 91 (21), 82 (j), 81 (12), 79 (14), 77 (14), 67 ( l l ) , 65 (7), 55 ( l l ) , 53 (13), 51 (8), 44 (5), 43 (12), 41 (25). C1,,H,,03 (182,22) Rer.…”

Section: (-)-2a3a-dimethyl-perhydroisobenzofuran-4/3-ol ((-)-11)11)unclassified

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Über die absolute Konfiguration der Cantharsäure und des Palasonins

Peter

Snatzke

et al. 1974

Helvetica Chimica Acta

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The absolute configurations of (+ )-canthark acid, a chiral derivative of the achiral insect defensive substance cantharidin ( l ) , and of palasonin, a lower homologue of 1 occurring in the plant Buteafrondosa, were shown t o be representcd b y formulas 2 and 3, respectively (scheme 7). These results were obtained b y application of the Horeau method (table 7) on the (+)-cantharic acid dcrivatives ( + ) -5 , (-)-7, and ( -) . 11 (scheme 2), and the palasonin derivatives (+)-29 and (+)-SO (scheme 4 , as well as b y comparison of the chiroptical propzrties (tables 2 and 3) of a number of derivatives, prepared from either cantharic acid or palasonin. -Attempts t o incorporate various radioactively labelled precursors into palasonin (3), using young and adult plants, have been so far unsuccessful.

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“…5 mg (0,552 mmol) (61, 202 (loo), 111 (13), 109 (5). 93 (7), 91 (8), 77 (16), 67 (€9, 65 (5), 55 (17), 54 (8), 53 (12), 51 (6). 44 (S), 43 (16).…”

Section: Acetoxy-cyclohex-l(mentioning

confidence: 99%

Section: (-)-2a3a-dimethyl-perhydroisobenzofuran-4/3-ol ((-)-11)11)unclassified

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Über die absolute Konfiguration der Cantharsäure und des Palasonins

Peter

Snatzke

et al. 1974

Helvetica Chimica Acta

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The Retro–Diels–Alder Reaction PartI.CCDienophiles

Rickborn

1998

Organic Reactions

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The Diels–Alder (“DA”) reaction is so familiar to organic chemists that the retro‐Diels–Alder or retro‐diene reaction (hereafter “rDA”) requires no conceptual introduction. However, a working definition is needed to indicate the coverage of this review. The intent is to include all reported examples of the general skeletal process excluded in this chapter. Any of the atoms in the starting material (cycloadduct) may be carbon or heteroatom, and substituents on all positions are allowed. In addition, any bond order available to the element in any oxidation state is included, as well as bonding to non‐nearest neighbor atoms (bicyclics, etc.). The volume of literature required separation of this review into two parts. Part I covers all expelled C–C dienophiles, i.e. those reactions that generate a new carbon‐carbon double or triple bond in the dienophile that is formed. Part II, to appear later, covers those expelled dienophiles in which one or both atoms is a heteroatom. Certain specific topics are intentionally omitted. These are: rDA reactions invoked under mass spectral conditions; rDA reactions of polymeric substrates; Electrocyclic processes, some of which are arguably very similar to rDA reactions (these are not addressed unless needed for clarification of an rDA sequence); and a thorough discussion of homo‐rDA reactions. CAS‐Online searches resulted in ca. 1,300 references, of which ca. 900 proved pertinent to the rDA topic as defined and delimited above. Active literature searching was halted in April 1995, but occasional more recent articles are included. Over 2,500 pertinent references were eventually found. Most were obtained by perusal of primary literature (articles) and secondary sources (books and reviews). Computer based search success was limited mainly by the failure of authors or abstractors to key‐word this topic, an especially common occurrence when the expelled dienophile was a simple substance such as N 2 or CO 2 . Overall, approximately 3,500 books, chapters, reviews, articles, and abstracts were consulted in an effort to make this review as comprehensive as possible. This was done with the certainty that some pertinent literature would be missed, tempered by the view that these omissions are probably also lost to any future rational search method. Many secondary sources proved valuable not only for in‐depth discussion of certain rDA reaction types, but also for providing comparisons with related topics. To assist the reader, these secondary sources are referenced (alphabetically by first author within broad subject areas) with a title or brief note on the topic(s) addressed. The first group lists earlier reviews with primary focus on rDA reactions, followed by items of Historical/General Interest, reviews that deal with Experimental Methods, DA reactions (general and specific), reviews of Related Topics (these impinge in more or less significant ways on rDA reactions), and general treatments of Theory and Mechanism.

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Catalytic Asymmetric (4 + 3) Cycloadditions Using Allenamides

Hsung

2012

Asymmetric Synthesis II

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Zur Konstitution des Kantharidins. Eine eigenartige Zerfallsreaktion des Kantharidins

Cited by 28 publications

References 0 publications

Über die absolute Konfiguration der Cantharsäure und des Palasonins

Über die absolute Konfiguration der Cantharsäure und des Palasonins

The Retro–Diels–Alder Reaction PartI.CCDienophiles

Catalytic Asymmetric (4 + 3) Cycloadditions Using Allenamides

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