A second-generation total synthesis of (+)-phorboxazole A

The Journal of Organic Chemistry
Amos B SmithRegina M Meis

Abstract

A highly convergent second-generation synthesis of (+)-phorboxazole A has been achieved. Highlights of the synthetic approach include improved Petasis-Ferrier union/rearrangement conditions on a scale to assemble multigram quantities of the C(11-15) and C(22-26) cis-tetrahydropyrans inscribed with the phorboxazole architecture, a convenient method to prepare E- and Z-vinyl bromides from TMS-protected alkynes utilizing radical isomerization of Z-vinylsilanes, and a convergent late-stage Stille union to couple a fully elaborated C(1-28) macrocyclic iodide with a C(29-46) oxazole stannane side chain to establish the complete phorboxazole skeleton. The synthesis, achieved with a longest linear sequence of 24 steps, proceeded in 4.6% overall yield.

References

Jul 18, 2001·Journal of the American Chemical Society·A B SmithM Schelhaas
Nov 1, 2001·Journal of the American Chemical Society·A B SmithM Schelhaas
May 10, 2002·Organic Letters·Guy D Joly, Eric N Jacobsen
Mar 20, 2003·Angewandte Chemie·Miguel A González, Gerald Pattenden
Mar 20, 2003·Angewandte Chemie·David R WilliamsJonathan T Reeves
Dec 20, 2003·Organic & Biomolecular Chemistry·Gerald PattendenTao Ye
Aug 12, 2004·Journal of the American Chemical Society·Ramesh JastiScott D Rychnovsky
Aug 28, 2004·Organic Letters·Brian S LucasSteven D Burke
Oct 14, 2004·Organic & Biomolecular Chemistry·Ian PatersonChris A Luckhurst
Nov 4, 2005·Chemistry : a European Journal·De-Run LiGuo-Qiang Lin
Mar 23, 2006·Journal of the American Chemical Society·Craig J ForsythJames J La Clair
Dec 14, 2006·Angewandte Chemie·Brian S LucasSteven D Burke
Dec 15, 2006·Organic Letters·James D WhiteTae Hee Lee
Dec 15, 2006·Organic Letters·James D WhitePunlop Kuntiyong

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Citations

Jul 30, 2009·Organic Letters·Amos B SmithTadeusz F Molinski
Jun 19, 2009·Briefings in Functional Genomics & Proteomics·Robert-Jan Theo Sijtse Palstra
Dec 9, 2010·Marine Drugs·Danilo Davyt, Gloria Serra
Mar 10, 2016·The Journal of Antibiotics·Zachary Shultz, James W Leahy
Jul 2, 2010·Natural Product Reports·Jonathan C Morris, Andrew J Phillips
Apr 8, 2011·Natural Product Reports·Zhong Jin
Apr 4, 2009·Organic Letters·Doralyn S Dalisay, Tadeusz F Molinski
Feb 13, 2009·Journal of the American Chemical Society·Daisuke ShikanaiHirokazu Urabe
Dec 31, 2010·Journal of the American Chemical Society·Bo WangCraig J Forsyth
Dec 31, 2010·Journal of the American Chemical Society·Bo WangCraig J Forsyth
Apr 4, 2015·Organic Letters·Alena S PankovaMikhail A Kuznetsov
Jun 19, 2013·The Journal of Organic Chemistry·Guo-Jie JiangZhi-Xiang Yu
Apr 29, 2015·Organic Letters·Justyna Szudkowska-FrątczakPiotr Pawluć

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