Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route

TY - JOUR

T1 - Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route

AU - Bastin, Reyhan

AU - Dale, James W.

AU - Edwards, Michael G.

AU - Papillon, Julien P. N.

AU - Webb, Michael R.

AU - Taylor, Richard J. K.

PY - 2011/12/23

Y1 - 2011/12/23

N2 - A formal synthesis of neooxazolomycin is described via the preparation of Kende's key intermediate in a longest linear sequence of 23 steps. This work is founded upon the union of three fragments: Moloney's lactam-derived triflate, a vinyl stannane and a Julia-Kocienski sulfone and encompasses three key steps: (i) a Stille cross-coupling to combine the triflate and vinyl stannane, (ii) a base-promoted enone deconjugation to derive the dihydroxylation precursor and (iii) our previously reported Julia-Kocienski methodology to assemble the pentadienyl amine side chain with the sulfone precursor. (C) 2011 Elsevier Ltd. All rights reserved.

AB - A formal synthesis of neooxazolomycin is described via the preparation of Kende's key intermediate in a longest linear sequence of 23 steps. This work is founded upon the union of three fragments: Moloney's lactam-derived triflate, a vinyl stannane and a Julia-Kocienski sulfone and encompasses three key steps: (i) a Stille cross-coupling to combine the triflate and vinyl stannane, (ii) a base-promoted enone deconjugation to derive the dihydroxylation precursor and (iii) our previously reported Julia-Kocienski methodology to assemble the pentadienyl amine side chain with the sulfone precursor. (C) 2011 Elsevier Ltd. All rights reserved.

UR - http://www.scopus.com/inward/record.url?scp=81255185086&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2011.09.037

DO - 10.1016/j.tet.2011.09.037

M3 - Article

SN - 0040-4020

VL - 67

SP - 10026

EP - 10044

JO - Tetrahedron

JF - Tetrahedron

IS - 51

ER -