Total synthesis of (+)-discodermolide: a highly convergent fourth-generation approach

Amos B Smith, 3rd; B Scott Freeze; Ming Xian; Tomoyasu Hirose

doi:10.1021/ol050455z

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Total synthesis of (+)-discodermolide: a highly convergent fourth-generation approach

Journal article

Peer reviewed

Total synthesis of (+)-discodermolide: a highly convergent fourth-generation approach

Amos B Smith, 3rd, B Scott Freeze, Ming Xian and Tomoyasu Hirose

Organic letters, Vol.7(9), pp.1825-1828

04/28/2005

DOI: https://doi.org/10.1021/ol050455z

Handle:

https://hdl.handle.net/2376/117553

PMID: 15844916

Abstract

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[structure: see text] A highly convergent, fourth-generation total synthesis of (+)-discodermolide (1), with a longest linear sequence of 17 steps and an overall yield of 9.0%, has been achieved. Highlighting the strategy is the efficient construction and sequential, bidirectional union of a linchpin comprising the C(9)-C(14) Wittig salt-vinyl iodide (-)-18. Importantly, Wittig salt generation proceeded in excellent yield under ambient pressure.

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Title: Total synthesis of (+)-discodermolide: a highly convergent fourth-generation approach
Creators: Amos B Smith, 3rd - Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
B Scott Freeze
Ming Xian
Tomoyasu Hirose
Publication Details: Organic letters, Vol.7(9), pp.1825-1828
Academic Unit: Chemistry, Department of
Publisher: United States
Grant note: GM-29028 / NIGMS NIH HHS
Identifiers: 99900548033901842
Language: English
Resource Type: Journal article

Total synthesis of (+)-discodermolide: a highly convergent fourth-generation approach

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