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Total synthesis of spirastrellolide A methyl ester--part 2: Subunit union and completion of the synthesis.

Abstract:

(Figure Presented) Succumbing to synthesis: The stereocontrolled total synthesis of spirastrellolide A methyl ester is reported. The union of two key C1-C16 and C17-C40 subunits is followed by macrolactonization and late-stage side chain attachment by a cross-metathesis reaction anda π-allyl Stille coupling reaction with a C43-C47 stannane, thus confirming the 46R configuration. The full configuration and conformation of the 38-membered macrolide is revealed by single-crystal X-ray analysis o...

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Publication status:
Published

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Publisher copy:
10.1002/anie.200705566

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Journal:
Angewandte Chemie (International ed. in English)
Volume:
47
Issue:
16
Pages:
3021-3025
Publication date:
2008-01-01
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
URN:
uuid:6f5b6d18-b95e-452d-adf4-0b85e9bab679
Source identifiers:
117841
Local pid:
pubs:117841

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