A biomimetically inspired, efficient synthesis of the South 7 hemisphere of cephalostatin 7.

A biomimetically inspired, efficient synthesis of the South 7 hemisphere of cephalostatin 7. Research Abstract Details 

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A biomimetically inspired, efficient synthesis of the South 7 hemisphere of cephalostatin 7. Abstract Text:

Jong Seok Lee,Philip L Fuchs,

Synthesis of the South 7 hemisphere of cephalostatin 7 is described applying a second-generation synthetic strategy, which retains all the existing carbons in hecogenin acetate 1. TFAT (trifluoroacetyl trifluoromethanesulfonate)-assisted E-ring opening yields the key D-ring cyclopentadiene. A facially selective [4 + 2] cycloaddition between a series of steroidal D-ring dienes and singlet oxygen was conformationally directed by the C21-Me stereochemistry of the side chain. Sharpless asymmetric dihydroxylation of the terminal olefin provides (S)-C25-OH. An acid-catalyzed SN2' intramolecular alkylation of an acetal oxygen was followed by a one-pot sequence of beta-elimination and spiroketalization. The new route provides a practical 16-operation synthesis of the South 7 hemisphere (20% overall), as well as a model for construction of the crucial North 1 hemisphere.

A biomimetically inspired, efficient synthesis of the South 7 hemisphere of cephalostatin 7. Publishing Authors By Initials

JS Lee,PL Fuchs,

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

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A biomimetically inspired, efficient synthesis of the South 7 hemisphere of cephalostatin 7. Journal Published:

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

Journal: Journal of the American Chemical Society

VOLUME: 127

Page Numbers: 13122-3

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 28

MONTH: Sep

YEAR: 2005

A biomimetically inspired, efficient synthesis of the South 7 hemisphere of cephalostatin 7. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

A biomimetically inspired, efficient synthesis of the South 7 hemisphere of cephalostatin 7. Keywords Mesh Terms:

KEYWORDS: Steroids

MESH TERMS: chemistry

Chemical & Substance for Abstract: A biomimetically inspired, efficient synthesis of the South 7 hemisphere of cephalostatin 7. Information

Substance Name: Singlet Oxygen

Registry Number: 17778-80-2

Grant and Affiliation Information for A biomimetically inspired, efficient synthesis of the South 7 hemisphere of cephalostatin 7.

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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