From Acyclic Intramolecular-[4+2]- to Transannular Bis-[4+2]-Cycloaddition of the Macrodiolide for the Stereoselective Synthesis of the Octahydronaphthalene Core of Polyenic Macrolactam Sagamilactam

被引：2
|
作者：
Iglesias-Menduina, Oscar [1 ]
Novegil, Diego [1 ]
Martinez, Claudio [1 ]
Alvarez, Rosana [1 ]
de Lera, Angel R. [1 ]
机构：
[1] Univ Vigo, Dept Quim Inorgan, CINBIO, 36310 Vigo, Spain
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 31期
关键词：
MACROLIDES; REAGENTS;
D O I：
10.1021/acs.orglett.4c02239
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The strategy for the synthesis of the octahydronaphthalene core of natural macrolide sagamilactam has unintentionally evolved from the acyclic intramolecular (IMDA) to the transannular (TADA) Diels-Alder reaction. Lewis acid-promoted IMDA of a protected 2Z,8E,10E-4,6,12-trihydroxy-2,8,10-decatrienal model with a diol of 4,6-anti relative configuration, as proposed by DP4+-based computational studies, afforded the cis-octahydronaphthalene diastereomer through the Re-endo approach. The 26-membered macrodiolide generated, under thermal reaction conditions, the trans-octahydronaphthalene by a double TADA reaction along the desired Si-exo orientation.
引用
收藏
页码：6614 / 6618
页数：5
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