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The total synthesis of (+)-aspicilin using 2,3-butane diacetal protected butane tetrols via a chiral memory protocol

Abstract:

The total syntheses of the polyhydroxylated macrolactone (+)-aspicilin and a diastereoisomer have been achieved via a concise route, starting from the spatially desymmetrized (R′,R′,R,S)-2,3-butanediacetal-protected butane tetrol 13. The key steps include a regioselective silyl protection of 13 and a stereoselective Lewis acid mediated addition of allyltributylstannane to the equatorially disposed aldehyde of 4. Macrocyclization is achieved using ring closing metathesis, after which selective...

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Publication status:
Published

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Publisher copy:
10.1139/cjc-79-11-1668

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE More from this journal
Volume:
79
Issue:
11
Pages:
1668-1680
Publication date:
2001-11-01
DOI:
ISSN:
0008-4042
Language:
English
Keywords:
Pubs id:
pubs:52086
UUID:
uuid:cc9290bc-4691-461d-ba7f-87fc75371186
Local pid:
pubs:52086
Source identifiers:
52086
Deposit date:
2012-12-19

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