Diastereoselective synthesis of the A-B-C tricyclic ring structure of stemocurtisine

Xuan Duc Dau; Anthony C. Willis; Stephen G. Pyne

doi:10.1002/ejoc.201501080

Diastereoselective synthesis of the A-B-C tricyclic ring structure of stemocurtisine

Xuan Duc Dau
, Anthony C. Willis
, Stephen G. Pyne^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

The diastereoselective synthesis of the A-B-C tricyclic ring structure of the Stemona alkaloid stemocurtisine is described. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide. Attempts to prepare the C-3a-C-11 ether moiety of this alkaloid through a photochemically induced oxidative cyclization method were unsuccessful because of the cleavage of the A-ring. The diastereoselective synthesis of the A-B-C tricyclic ring structure of the Stemona alkaloid stemocurtisine has been developed. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide (TBS = tert-butyldimethylsilyl).

Original language	English
Pages (from-to)	7682-7694
Number of pages	13
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	35
DOIs	https://doi.org/10.1002/ejoc.201501080
Publication status	Published - 1 Dec 2015

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title = "Diastereoselective synthesis of the A-B-C tricyclic ring structure of stemocurtisine",

abstract = "The diastereoselective synthesis of the A-B-C tricyclic ring structure of the Stemona alkaloid stemocurtisine is described. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide. Attempts to prepare the C-3a-C-11 ether moiety of this alkaloid through a photochemically induced oxidative cyclization method were unsuccessful because of the cleavage of the A-ring. The diastereoselective synthesis of the A-B-C tricyclic ring structure of the Stemona alkaloid stemocurtisine has been developed. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide (TBS = tert-butyldimethylsilyl).",

keywords = "Alkaloids, Cyclization, Diastereoselectivity, Epoxidation, Natural products, Nitrogen heterocycles",

author = "Dau, \{Xuan Duc\} and Willis, \{Anthony C.\} and Pyne, \{Stephen G.\}",

note = "Publisher Copyright: Copyright {\textcopyright} 2015 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

year = "2015",

month = dec,

day = "1",

doi = "10.1002/ejoc.201501080",

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volume = "2015",

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journal = "European Journal of Organic Chemistry",

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T1 - Diastereoselective synthesis of the A-B-C tricyclic ring structure of stemocurtisine

AU - Dau, Xuan Duc

AU - Willis, Anthony C.

AU - Pyne, Stephen G.

PY - 2015/12/1

Y1 - 2015/12/1

N2 - The diastereoselective synthesis of the A-B-C tricyclic ring structure of the Stemona alkaloid stemocurtisine is described. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide. Attempts to prepare the C-3a-C-11 ether moiety of this alkaloid through a photochemically induced oxidative cyclization method were unsuccessful because of the cleavage of the A-ring. The diastereoselective synthesis of the A-B-C tricyclic ring structure of the Stemona alkaloid stemocurtisine has been developed. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide (TBS = tert-butyldimethylsilyl).

AB - The diastereoselective synthesis of the A-B-C tricyclic ring structure of the Stemona alkaloid stemocurtisine is described. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide. Attempts to prepare the C-3a-C-11 ether moiety of this alkaloid through a photochemically induced oxidative cyclization method were unsuccessful because of the cleavage of the A-ring. The diastereoselective synthesis of the A-B-C tricyclic ring structure of the Stemona alkaloid stemocurtisine has been developed. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide (TBS = tert-butyldimethylsilyl).

KW - Alkaloids

KW - Cyclization

KW - Diastereoselectivity

KW - Epoxidation

KW - Natural products

KW - Nitrogen heterocycles

UR - https://www.scopus.com/pages/publications/84948154868

U2 - 10.1002/ejoc.201501080

DO - 10.1002/ejoc.201501080

M3 - Article

SN - 1434-193X

VL - 2015

SP - 7682

EP - 7694

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 35

ER -

Diastereoselective synthesis of the A-B-C tricyclic ring structure of stemocurtisine

Abstract

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