Dyotropic rearrangement facilitated proximal functionalization and oxidative removal of angular methyl groups: efficient syntheses of 23'-deoxy cephalostatin 1 analogues.

Dyotropic rearrangement facilitated proximal functionalization and oxidative removal of angular methyl groups: efficient syntheses of 23'-deoxy cephalostatin 1 analogues. Research Abstract Details 

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Dyotropic rearrangement facilitated proximal functionalization and oxidative removal of angular methyl groups: efficient syntheses of 23'-deoxy cephalostatin 1 analogues. Abstract Text:

Wei Li,Thomas G LaCour,P L Fuchs,

Oxidative functionalization (or removal) of a steroidal C18 methyl group is possible using a previously unknown dyotropic rearrangement of a seven-membered fused C-ring lactone to a 6-ring spiro lactone. Spiroketal equilibration led to the 23-deoxy South analogue of cephalostatin 1 (1) in only 12 steps (23% overall yield) from hecogenin acetate 4, and to strained diene South 1 analogue 30 in 11 steps (28% overall). Total synthesis of 23'-deoxy cephalostatin 1 (3) was accomplished in 16 operations from 4 (9% overall; average 86% yield per operation), and that of 16',17'-dehydro-23'-deoxy cephalostatin 1 (36) in 15 operations from 4 (8% overall; av 84%/op).

Dyotropic rearrangement facilitated proximal functionalization and oxidative removal of angular methyl groups: efficient syntheses of 23'-deoxy cephalostatin 1 analogues. Publishing Authors By Initials

W Li,TG LaCour,PL Fuchs,

For similar polycyclic compounds: steroids research abstracts see: polycyclic compounds: steroids research

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Dyotropic rearrangement facilitated proximal functionalization and oxidative removal of angular methyl groups: efficient syntheses of 23'-deoxy cephalostatin 1 analogues. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 124

Page Numbers: 4548-9

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 1

MONTH: May

YEAR: 2002

Dyotropic rearrangement facilitated proximal functionalization and oxidative removal of angular methyl groups: efficient syntheses of 23'-deoxy cephalostatin 1 analogues. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

Dyotropic rearrangement facilitated proximal functionalization and oxidative removal of angular methyl groups: efficient syntheses of 23'-deoxy cephalostatin 1 analogues. Keywords Mesh Terms:

KEYWORDS: Steroids

MESH TERMS: chemistry

Chemical & Substance for Abstract: Dyotropic rearrangement facilitated proximal functionalization and oxidative removal of angular methyl groups: efficient syntheses of 23'-deoxy cephalostatin 1 analogues. Information

Substance Name: Spironolactone

Registry Number: 52-01-7

Grant and Affiliation Information for Dyotropic rearrangement facilitated proximal functionalization and oxidative removal of angular methyl groups: efficient syntheses of 23'-deoxy cephalostatin 1 analogues.

AFFILIATION: Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.

Country: United States

AGENCY: United States NCI

GRANT: CA 60548

ACRONYM: CA

MEDLINETA: J Am Chem Soc

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