布鲁斯醇 D、E 和 J 的短保护基自由全合成

A short, protecting group-free total synthesis of bruceollines D, E, and J.

机构信息

Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.

出版信息

Org Lett. 2013 Sep 6;15(17):4485-7. doi: 10.1021/ol402042f. Epub 2013 Aug 12.

DOI:10.1021/ol402042f

Abstract

A short, protecting group-free total synthesis of bruceollines D, E, and J has been achieved. The enantioselective reduction of bruceolline E with β-chlorodiisopinocampheylborane delivers both the natural and unnatural enantiomers of bruceolline J in excellent yields and enantioselectivities. Reduction with baker's yeast and sucrose was shown to provide the unnatural enantiomer of bruceolline J in 98% ee.

摘要

已实现布鲁斯醇 D、E 和 J 的短保护基-自由全合成。用β-氯二异松蒎基硼烷对布鲁斯醇 E 进行对映选择性还原，以优异的收率和对映选择性得到了布鲁斯醇 J 的天然和非天然对映异构体。用贝克氏酵母和蔗糖还原得到了布鲁斯醇 J 的非天然对映异构体，ee 值为 98%。