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. 2018 Jan 22;8(7):3899-3902.
doi: 10.1039/c7ra13391j. eCollection 2018 Jan 16.

Synthesis of C14-C21 acid fragments of cytochalasin Z8 via anti-selective aldol condensation and B-alkyl Suzuki-Miyaura cross-coupling

Weiwei Han  1   2
Affiliations

Synthesis of C14-C21 acid fragments of cytochalasin Z8 via anti-selective aldol condensation and B-alkyl Suzuki-Miyaura cross-coupling

Weiwei Han. RSC Adv. .

Erratum in

Abstract

An efficient synthesis of the C14-C21 acid fragment of cytochalasin Z8 was accomplished in 10 steps with 14% overall yield. Boron-mediated anti-selective aldol condensation and Pd(OAc)2-Aphos-Y-catalysed B-alkyl Suzuki-Miyaura cross-coupling were employed to construct the requisite C17 and C18 stereogenic centres and alkene subunit.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Chart 1
Chart 1. Structures of cytochalasin Z7–Z9.
Scheme 1
Scheme 1. Retrosynthetic bond disconnections of cytochalasin Z8 (2) yielding C14–C21 acid fragment 4 and hydroisoindol-1-one fragment.
Scheme 2
Scheme 2. Synthesis of alkyl iodide 6.
Scheme 3
Scheme 3. Cross-coupling of chiral alkyl iodide 5 with (Z)-1-bromoprop-1-ene.
Scheme 4
Scheme 4. Synthesis of C14–C21 acid fragment 4.
See this image and copyright information in PMC

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