Thieme Chemistry Journal Awardees - Where Are They Now? Stereoselective Synthesis of Z-Configured α,β-Unsaturated Macrocyclic Lactones and Diolides by Intramolecular Julia-Kocienski Olefination
Thieme Chemistry Journal Awardees - Where Are They Now? Stereoselective Synthesis of Z-Configured α,β-Unsaturated Macrocyclic Lactones and Diolides by Intramolecular Julia-Kocienski Olefination
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DOI：
10.1055/s-0029-1219185
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发表时间：
2010-02-01
期刊：
影响因子：
2
通讯作者：
Blakemore, Paul R.
中科院分区：
文献类型：
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作者：
Giesbrecht, Heath E.;Knight, Brian J.;Blakemore, Paul R.
(苯并噻唑-2-基磺酰基)乙酸与欧米伽-烯醇或α-欧米茄二醇酯化，再经臭解或Dess-Martin氧化得到的欧米磺酰醛在DBU的作用下发生了分子内Julia-Kocienski烯化反应。使用该策略成功地形成了12-和19-元环尺寸之间的大环α，β-不饱和内酯(产率24-44%，Z/E>；=3.5：1)；然而，二内酯是从以7-9元环内酯为目标的前体选择性地生成的(产率13-70%，ZZ/z>；=2：1)。
omega-Sulfonyl aldehydes derived from the esterification of (benzothiazol-2-ylsulfonyl) acetic acid with either omega-alkenols or alpha,omega-diols, followed by ozonolysis or Dess-Martin oxidation as appropriate, underwent intramolecular Julia-Kocienski olefination when treated with DBU. Macrocyclic alpha,beta-unsaturated lactones of between 12- and 19-membered ring sizes were formed successfully using this tactic (24-44% yield, Z/E >= 3.5:1); however, diolides were selectively produced from precursors intended to target seven- to nine-membered-ring lactones (13-70% yield, ZZ/ZE >= 2:1).