Terpene und terpen-derivate—vii

Hoppmann, A.; Weyerstahl, Peter

doi:10.1016/0040-4020(78)80208-7

Cited by 32 publications

(8 citation statements)

References 21 publications

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“…Other desulfurisation methods (Na, NH 3 and Bu 3 SnH, AIBN respectively) 25,26 were unsatisfactory giving only a trace of the desired product 9.…”

Section: Methodsmentioning

confidence: 99%

Pheromones of Pine Sawflies: Synthesis of a Pure (2S,3R)-3-Methylalkan-2-ol Stereoisomer via an Asymmetric 1,3-Dipolar Cycloaddition; Preparation of a Pheromone Component of Macrodiprion nemoralis

Karlsson¹,

Högberg²

2000

Synthesis

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This paper presents a new approach to the preparation of enantiomerically pure (2S,3R)-3-methylalkan-2-ols, the esters of which are sex pheromones of several pine sawflies. Thus, an asymmetric 1,3-dipolar cycloaddition between a sulfur containing 1,3-dipole and a dipolarophile attached to (1R)-camphorsultam containing a vinyl ether functionality furnished a 90:10 diastereomeric mixture of trans-3,4-disubstituted tetrahydrothiophene amides. The major one was converted to an enantiomerically pure tetrahydrothienylmethyl bromide, which was coupled with a monoalkylated dithiane unit. After Raney nickel reduction (2S,3R,7R,9S)-3,7,9-trimethyltridecan-2-ol was obtained, the acetate of which is the attractant sex pheromone component of Macrodiprion nemoralis. Because this new approach is quite efficient it can be valuable for the synthesis of similar compounds.

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“…Other desulfurisation methods (Na, NH 3 and Bu 3 SnH, AIBN respectively) 25,26 were unsatisfactory giving only a trace of the desired product 9.…”

Section: Methodsmentioning

confidence: 99%

Pheromones of Pine Sawflies: Synthesis of a Pure (2S,3R)-3-Methylalkan-2-ol Stereoisomer via an Asymmetric 1,3-Dipolar Cycloaddition; Preparation of a Pheromone Component of Macrodiprion nemoralis

Karlsson¹,

Högberg²

2000

Synthesis

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“…The syntheses of compounds belonging to this group of furan monoterpenoids have been accomplished by various methods. Egomaketone [2] has been prepared via 3-cyanofuran (5,6), 3-furoyl chloride (7), 3 -furancarbaldehyde (8), 2-(3-furyl)-1,3-dithiane (9), and 3furyltrimethyltin (10), using 3-bromofuran as starting material. However, some of these syntheses involve many steps and others use expensive reagents to introduce a side-chain onto the 3-position of furan.…”

Section: A Short Synthesis Of 4-(3-furyl)-4-oxobutanoic Acid and Synt...mentioning

confidence: 99%

A Short Synthesis of 4-(3-Furyl)-4-oxobutanoic Acid and Synthesis of Egomaketone

Koyanagi¹,

Yamamoto²,

Nakayama³

1995

J. Nat. Prod.

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“…Accordingly, cleavage of the dithioacetal group was performed under mild conditions with an HgO/HgCl 2 mixture in acetone/ water, followed by treatment with an aqueous solution of KI. [32] The expected aldehyde 25 was thus isolated and applied in the subsequent step without any purification. JuliaϪKocienski olefination [33] was used to generate the second side chain double bond.…”

mentioning

confidence: 99%

A Stereoselective Formal Synthesis of (−)‐Fumagillol

Bedel¹,

Haudrechy²,

Langlois³

2004

Eur J Org Chem

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A novel formal synthesis of fumagillol, a direct precursor of the antiangiogenic sesquiterpene fumagillin, is described. The main features of the synthesis are a stereoselective Claisen−Ireland rearrangement, a ring-closing metathesis, a Fumagillin (1), isolated in 1951 by Elbe and Hanson [1] from the microbial organism Aspergillus fumigatus, is representative of a class of sesquiterpenes like ovalicin (2) [2] and FR 65814 (3), [3] which display various biological activities. Fumagillin (1) was originally described as an antimicrobial agent, but Folkman and co-workers [4] have more recently discovered that this compound is a potent and selective inhibitor of angiogenesis. The semisynthetic compound TNP-470 (4) [5,6] showed a better therapeutic index than fumagillin (1) and is one of the most promising drugs acting as an inhibitor of angiogenesis (Scheme 1). Scheme 1The recent discovery that methionine aminopeptidase II (MetAp-II) is selectively inhibited by fumagillin (1), [7] together with the X-ray structure of the covalent complex between fumagillin (1) and MetAp-II, [8] have increased interest in the synthesis of fumagillin (1) and of new fumagillin analogues.[9Ϫ11] [a]

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Terpene und terpen-derivate—vii

Cited by 32 publications

References 21 publications

Pheromones of Pine Sawflies: Synthesis of a Pure (2S,3R)-3-Methylalkan-2-ol Stereoisomer via an Asymmetric 1,3-Dipolar Cycloaddition; Preparation of a Pheromone Component of Macrodiprion nemoralis

Pheromones of Pine Sawflies: Synthesis of a Pure (2S,3R)-3-Methylalkan-2-ol Stereoisomer via an Asymmetric 1,3-Dipolar Cycloaddition; Preparation of a Pheromone Component of Macrodiprion nemoralis

A Short Synthesis of 4-(3-Furyl)-4-oxobutanoic Acid and Synthesis of Egomaketone

A Stereoselective Formal Synthesis of (−)‐Fumagillol

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