Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 34, Pages 10838-10841Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b07585
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Funding
- NSF [CAREER 1553820]
- ACS Petroleum Research Foundation (PRF) [54896-DNI1]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1553820] Funding Source: National Science Foundation
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Spinosyn A (1), a complex natural product featuring, a unique 5,6,5,12-fused tetracyclic core structure, is the major component of spinosad, an organic insecticide and an FDA-approved agent used worldwide. Herein, we report an efficient total synthesis of (-)-spinosyn A with 15 steps in the longest linear sequence and 23 steps total from readily available compounds 14 and 23. The synthetic approach features several important catalytic transformations including a chiral amine-catalyzed intramolecular Diels- Alder reaction to afford 22 in excellent diastereoselectivity, a One-step gold-catalyzed propargylic acetate rearrangement to convert 28 to alpha-iodoenone 31, an unprecedented palladium-catalyzed carbonylative Heck macrolactonization to form the 5,12-fused macrolactone in one step, and a gold-catalyzed Yu glycosylation to install the challenging beta-forosamine. This total synthesis is highly convergent and: modular, thus offering opportunities to synthesize spinosyn analogues in order to address the emerging cross-resistance problems.
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