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First Total Synthesis of Varioxiranol A.

ABSTRACT: 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?Kocie?ski coupling reaction between aromatic sulfone and corresponding aldose derivative makes it possible to prepare other interesting polyketide derivatives (varioxiranols B-G, varioxirane, varioxiranediols).

SUBMITTER: Lasikova A

PROVIDER: S-EPMC6429112 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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First Total Synthesis of Varioxiranol A.

Lásiková Angelika A Doháňošová Jana J Štiblariková Mária M Parák Martin M Moncol Ján J Gracza Tibor T

Molecules (Basel, Switzerland) 20190228 5

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-<i>O</i>-isopropylidene-d-glyceraldehyde in an overall yield of 10% and 6%, respectively. A synthetic strategy based on the Julia⁻Kocieński coupling reaction between aromatic sulfone and corresponding aldose ...[more]

PMID: 30823483

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