Convergent assembly of the spiroacetal subunit of didemnaketal B

Haruhiko Fuwa; Sayaka Noji; Makoto Sasaki

doi:10.1021/ol1024713

Convergent assembly of the spiroacetal subunit of didemnaketal B

Haruhiko Fuwa, Sayaka Noji, Makoto Sasaki

LIF - Molecular and Chemical Life Science

Tohoku University

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

A highly convergent synthesis of the C9-C28 spiroacetal subunit of didemnaketal B has been accomplished. Assembly of the C9-C15 alkylborate and C16-C21 enol phosphate by means of Suzuki-Miyaura coupling and acid-catalyzed cyclization of the derived dihydroxy enol ether enabled a rapid and efficient construction of the spiroacetal subunit. The C22-C28 side chain was incorporated via Nozaki-Hiyama-Kishi coupling to complete the synthesis.

Original language	English
Pages (from-to)	5354-5357
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	22
DOIs	https://doi.org/10.1021/ol1024713
Publication status	Published - 2010 Nov 19

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10.1021/ol1024713

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abstract = "A highly convergent synthesis of the C9-C28 spiroacetal subunit of didemnaketal B has been accomplished. Assembly of the C9-C15 alkylborate and C16-C21 enol phosphate by means of Suzuki-Miyaura coupling and acid-catalyzed cyclization of the derived dihydroxy enol ether enabled a rapid and efficient construction of the spiroacetal subunit. The C22-C28 side chain was incorporated via Nozaki-Hiyama-Kishi coupling to complete the synthesis.",

author = "Haruhiko Fuwa and Sayaka Noji and Makoto Sasaki",

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AU - Fuwa, Haruhiko

AU - Noji, Sayaka

AU - Sasaki, Makoto

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N2 - A highly convergent synthesis of the C9-C28 spiroacetal subunit of didemnaketal B has been accomplished. Assembly of the C9-C15 alkylborate and C16-C21 enol phosphate by means of Suzuki-Miyaura coupling and acid-catalyzed cyclization of the derived dihydroxy enol ether enabled a rapid and efficient construction of the spiroacetal subunit. The C22-C28 side chain was incorporated via Nozaki-Hiyama-Kishi coupling to complete the synthesis.

AB - A highly convergent synthesis of the C9-C28 spiroacetal subunit of didemnaketal B has been accomplished. Assembly of the C9-C15 alkylborate and C16-C21 enol phosphate by means of Suzuki-Miyaura coupling and acid-catalyzed cyclization of the derived dihydroxy enol ether enabled a rapid and efficient construction of the spiroacetal subunit. The C22-C28 side chain was incorporated via Nozaki-Hiyama-Kishi coupling to complete the synthesis.

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JO - Organic Letters

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Convergent assembly of the spiroacetal subunit of didemnaketal B

Abstract

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