骈合组装二倍半萜内酯 didemnaketal B 的螺缩酮亚单位。

Convergent assembly of the spiroacetal subunit of didemnaketal B.

机构信息

Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.

出版信息

Org Lett. 2010 Nov 19;12(22):5354-7. doi: 10.1021/ol1024713. Epub 2010 Oct 28.

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.

摘要

已完成 didemnaketal B 的 C9-C28 螺缩酮亚基的高收率综合。通过 Suzuki-Miyaura 偶联以及衍生的二羟乙氧基的酸催化环化，将 C9-C15 烷基硼酸酯和 C16-C21 烯醇磷酸酯组装在一起，能够快速有效地构建螺缩酮亚基。通过 Nozaki-Hiyama-Kishi 偶联引入 C22-C28 侧链，完成了全合成。