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

A second-generation total synthesis of (+)-phorboxazole a. Research Abstract Details 

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A second-generation total synthesis of (+)-phorboxazole a. Abstract Text:

Amos B Smith,Thomas M Razler,Jeffrey P Ciavarri,Tomoyasu Hirose,Tomoyasu Ishikawa,Regina M Meis,Amos B Smith,Thomas M Razler,Jeffrey P Ciavarri,Tomoyasu Hirose,Tomoyasu Ishikawa,Regina M Meis,

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.

A second-generation total synthesis of (+)-phorboxazole a. Publishing Authors By Initials

AB Smith,TM Razler,JP Ciavarri,T Hirose,T Ishikawa,RM Meis,AB Smith,TM Razler,JP Ciavarri,T Hirose,T Ishikawa,RM Meis,

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A second-generation total synthesis of (+)-phorboxazole a. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: The Journal of organic chemistry

VOLUME: 73

Page Numbers: 1192-200

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 24

MONTH: 01

YEAR: 2008

A second-generation total synthesis of (+)-phorboxazole a. Information

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LANGUAGE: eng

NlmUniqueID: 2985193

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Grant and Affiliation Information for A second-generation total synthesis of (+)-phorboxazole a.

AFFILIATION: Department of Chemistry, The Penn Center for Molecular Discovery, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104.

Country: United States

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MEDLINETA: J Org Chem

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