Total Synthesis of the Proposed Structure of Briarellin J

被引：30

作者：

Crimmins, Michael T. ^{[1
]}

Mans, Mark C. ^{[1
]}

Rodriguez, Abimael D. ^{[2
]}

机构：

[1] Univ N Carolina, Kenan Caudill Venable & Murray Labs Chem, Chapel Hill, NC 27599 USA

[2] Univ Puerto Rico, Dept Chem, San Juan, PR 00931 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 21期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; RING-CLOSING METATHESIS; CORAL PACHYCLAVULARIA-VIOLACEA; EUNICELLIN-BASED DITERPENOIDS; INDIAN GORGONIAN CORAL; DIELS-ALDER APPROACH; ASBESTINUM PALLAS; NATURAL-PRODUCTS; OPHIRIN-B; STRATEGY;

D O I：

10.1021/ol102169w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.

引用

页码：5028 / 5031

页数：4

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