Bioinspired Total Synthesis of 3-epi-Junipercedrol

被引：1

作者：

Xiao, Jian ^{[1
]}

Liu, Zi-Hao ^{[2
]}

He, Zi-Fan ^{[1
]}

Wu, Ping ^{[1
]}

Wang, Ya-Wen ^{[1
]}

Li, Wei-Dong Z. ^{[1
]}

Peng, Yu ^{[1
]}

机构：

[1] Southwest Jiaotong Univ, Sch Chem, Key Lab Adv Technol Mat, Minist Educ, Chengdu 610031, Peoples R China

[2] Southwest Jiaotong Univ, Sch Life Sci & Engn, Key Lab Adv Technol Mat, Minist Educ,Sch Chem, Chengdu 610031, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 35期

基金：

中国国家自然科学基金;

关键词：

TRICYCLIC SESQUITERPENES; DERIVATIVES; MIGRATIONS;

D O I：

10.1021/acs.orglett.4c02877

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A bioinspired total synthesis of 3-epi-junipercedrol, which contains a strained tricyclo[5.2.2.0(3,7)]undecane allo-cedrane framework and five stereocenters, was accomplished via an effective anionic semipinacol rearrangement of a tricyclic cedrane mesylate. The corresponding cedrane precursor was synthesized efficiently by employing the reductive oxy-Nazarov cyclization and an intramolecular aldol condensation as the key steps. This synthetic approach provided a further evidence for the biogenetic relationship between the typical cedrane and allo-cedrane sesquiterpenoids.

引用

页码：7463 / 7467

页数：5

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