Journal
ORGANIC LETTERS
Volume 12, Issue 17, Pages 3752-3755Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol101340n
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Funding
- NIH [GM088839]
- NSF [CHE-0749451]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1114891] Funding Source: National Science Foundation
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A total synthesis of the fostriecin has been achieved in 24 steps from enyne 11. The lactone moiety was installed by a Leighton allylation and Grubbs ring-closing metathesis reaction. The highly reactive Z,Z,E-triene moiety was installed via a late-stage Suzuki-Miyaura cross-coupling of a remarkably stable Z-vinyl boronate. The relative and absolute stereocenters of the C-8,9,11 triol were generated with a regio- and stereoselective asymmetric hydration/oxidation sequence.
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