Synthesis of the C1-C17 segment of phorboxazole B

Organic Letters
Brian S LucasSteven D Burke

Abstract

The C1-C17 bis-oxane subunit 22 of phorboxazole B is efficiently synthesized by exploiting differential reactivities between similar substituents on the hydropyran rings in 4. Selective dihydroxylation of the equatorial vinyl group, hydroboration of the axial vinyl group, and intramolecular Mitsunobu lactonization serve to fully differentiate the similar hydropyrans.

References

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Citations

Apr 21, 2011·The Journal of Organic Chemistry·Rambabu ChegondiPaul R Hanson
May 3, 2011·The Journal of Organic Chemistry·Paul R HansonAlan Whitehead
Jun 3, 2006·Natural Product Reports·Zhong Jin
Nov 14, 2015·Journal of the American Chemical Society·John F Hartwig
Dec 14, 2006·Angewandte Chemie·Brian S LucasSteven D Burke
Nov 1, 2009·European Journal of Organic Chemistry·Christopher D ThomasPaul R Hanson
Nov 4, 2005·Chemistry : a European Journal·De-Run LiGuo-Qiang Lin
Oct 14, 2004·Organic & Biomolecular Chemistry·Ian PatersonChris A Luckhurst
Jan 25, 2008·The Journal of Organic Chemistry·Amos B SmithRegina M Meis
Dec 10, 2016·Journal of Natural Products·Birakishore PadhiDebendra K Mohapatra
Apr 23, 2005·The Journal of Organic Chemistry·Brian S LucasSteven D Burke
Dec 15, 2006·Organic Letters·James D WhiteTae Hee Lee

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