Synthetic studies on calyculin a: a convenient asymmetric synthesis of anti-vicinal diols
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 14,p. 1901-1905
- https://doi.org/10.1039/p19940001901
Abstract
anti-Vicinal diols have been prepared with excellent relative and absolute stereocontrol via the reaction of aldehydes with B-{3-[(diisopropylamino)dimethylsilyl]allyl}diisopinocampheylborane in THF and diethyl ether and work-up using potassium fluoride, potassium hydrogen carbonate and hydrogen peroxide in aqueous methanol. Absolute stereoselectivities of reactions were determined by conversion of four product diols into bis[(R)-α-methoxy-α-(trifluoromethyl)phenylacetate] esters. The reactions are relevant to the synthesis of the marine phosphatase inhibitor calyculin A.Keywords
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