Journal
MOLECULES
Volume 24, Issue 5, Pages -Publisher
MDPI
DOI: 10.3390/molecules24050862
Keywords
synthesis of natural products; varioxiranol A; 4-epi-varioxiranol A; absolute structure; Emericella variecolor
Funding
- VEGA [1/0552/18, APVV-14-0147]
- ASFU, Bratislava, ITMS projects [26240120025, 26240220084]
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The paper describes the first total synthesis of natural varioxiranol A by chiral pool approach and confirmation of its absolute configuration by single-crystal X-ray analysis. The target varioxiranol A and its 4-epimer were obtained after 10 steps from single and available chiral source 1,2-O-isopropylidene-D-glyceraldehyde in an overall yield of 10% and 6%, respectively. A synthetic strategy based on the Julia-Kocienski coupling reaction between aromatic sulfone and corresponding aldose derivative makes it possible to prepare other interesting polyketide derivatives (varioxiranols B-G, varioxirane, varioxiranediols).
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