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Issue 26, 2016
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Gold-catalyzed Hosomi–Sakurai type reaction for the total synthesis of herboxidiene

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Abstract

Total synthesis of herboxidiene/GEX1A/TAN-1609 has been accomplished in the 22 longest linear sequences starting from 2-butyne-1,4-diol following our recently developed gold-catalyzed Hosomi–Sakurai type of reaction on lactols with allyltrimethyl silane and Stille cross coupling to assemble the advanced fragment. The synthesis of the C10–C19 fragment was accomplished by means of Sharpless epoxidation and asymmetric alkylation reactions starting from (R)-methyl lactate.

Graphical abstract: Gold-catalyzed Hosomi–Sakurai type reaction for the total synthesis of herboxidiene

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Publication details

The article was received on 09 Feb 2016, accepted on 06 May 2016 and first published on 10 May 2016


Article type: Paper
DOI: 10.1039/C6OB00321D
Citation: Org. Biomol. Chem., 2016,14, 6212-6224

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    Gold-catalyzed Hosomi–Sakurai type reaction for the total synthesis of herboxidiene

    B. Thirupathi and D. K. Mohapatra, Org. Biomol. Chem., 2016, 14, 6212
    DOI: 10.1039/C6OB00321D

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