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

页码：6614 / 6618

页数：5

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