The total synthesis of some pyrrolyzidine alkaloids and their absolute configuration

Kochetkov, Nikolay K.; Лихошерстов, А. М.; Kulakov, V. N.

doi:10.1016/s0040-4020(01)82781-2

Cited by 27 publications

(8 citation statements)

References 20 publications

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“…1, (-)-supinine (12S,13R) and (-)-heleurine (12S,13R), have been assigned by comparison with that of supinidine, in agreement with the absolute configuration established by Kochetkov, Likhosherstov & Kulakov (1969) for (+)-trachelanthic (2S,3R) acid, the moiety in supinine, which has the same absolute configuration as heliotric acid, the acid moiety in heleurine.…”

Section: Discussion Final Atomic Coordinates Are Given Insupporting

confidence: 73%

Supinine, C15H25NO4, and heleurine, C16H27NO4, pyrrolizidine alkaloids

Mackay¹,

Mitrprachachon²,

Oliver³

et al. 1985

Acta Crystallogr C

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Section: Discussion Final Atomic Coordinates Are Given Insupporting

confidence: 73%

Supinine, C15H25NO4, and heleurine, C16H27NO4, pyrrolizidine alkaloids

Mackay¹,

Mitrprachachon²,

Oliver³

et al. 1985

Acta Crystallogr C

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“…[6] His strategy was based on diastereoselective dihydroxylations of (Z)-and (E)-isopropylcrotonic acid, furnishing either (Ϯ)-anti-7a or (Ϯ)-syn-7a. The (E)-isopropylcrotonic acid was synthesized in poor yield from ethyl 3-hydroxy-2-isopropylbutyrate.…”

Section: Synthesis Of Viridifloric β-Lactone (1a) and Its Nor Derivatmentioning

confidence: 99%

Absolute Configuration and Synthesis of β- and δ-Lactones Present in the Pheromone System of the Giant White Butterfly Idea leuconoe

2002

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Males of the giant white butterfly Idea leuconoe release a complex mixture of compounds during courtship. Besides alkaloids, aromatics, terpenoids and hydrocarbons, several lactones have been identified in the pheromone bouquet. Two simple stereoselective methods to create the lactones in good enantiomeric excesses have been developed. The generation of the stereocenters of the β-lactones 1a and 1b is based on a controlled C−C coupling by a Horner−Wadsworth−Emmons approach, followed by asymmetric dihydroxylation, whereas the synthesis of the δ-lactone 3b uses an enantioselective hy-

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“…The relative configuration of the lasiocarpic acid moiety has not been determined, although the decomposition of lasiocarpic acid, 2,3-dihydroxy-2-(l'-methoxyethyl)-3-methylbutanoic acid (III: R = OH), in hydrochloric acid to give (+)-2-methoxy-4-methyl-3-pentanone (IV) shows that lasiocarpic acid has the same absolute configuration at C(I') as heliotric acid, 2-hydroxy-2-(l'-methoxyethyl)-3-methylbutanoic acid (III:R = H) (Crowley & Culvenor, 1960). The absolute configuration of (-)-heliotric acid (Culvenor, Drummond & Price, 1954) has been established as (2S, I'R) by the chemical studies of Kochetkov, Likhosherstov & Kulakov (1969), and the relative configuration was confirmed from the X-ray crystal structure of heliotrine (I: R = R' = H) by Wodak (1975).…”

Section: Introductionmentioning

confidence: 95%

The structure of lasiocarpine: a pyrrolizidine alkaloid

Hay¹,

Mackay²,

Culvenor³

1982

Acta Crystallogr Sect B

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Orthorhombic crystals of the hepatotoxic pyrrolizidine alkaloid, lasiocarpine (C21H33NOT, M r = 411.5), crystallize in the space group P212~21, with a = 10.066 (2) least-squares refinement converged at R = 0.067 for 1396 observed reflections. Lasiocarpine is a di-ester which does not form a covalent macro-ring, and the relative configuration at the asymmetric centres in the molecule is the same as in the related alkaloid, heliotrine (CI6HETNOs). An intermolecular hydrogen bond involving one of the hydroxyl substituents and the N atom links the lasiocarpine molecules into helices extending along the b axis.

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The total synthesis of some pyrrolyzidine alkaloids and their absolute configuration

Cited by 27 publications

References 20 publications

Supinine, C15H25NO4, and heleurine, C16H27NO4, pyrrolizidine alkaloids

Supinine, C15H25NO4, and heleurine, C16H27NO4, pyrrolizidine alkaloids

Absolute Configuration and Synthesis of β- and δ-Lactones Present in the Pheromone System of the Giant White Butterfly Idea leuconoe

The structure of lasiocarpine: a pyrrolizidine alkaloid

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