Total Synthesis of the Myrioneuron Alkaloid (-)-Schoberine B and Its Enantiomer (+)-Schoberine B

被引：1

作者：

Calbo, Arnau ^{[1
,2
]}

Griera, Rosa ^{[1
,2
]}

Bosch, Joan ^{[1
,2
]}

Amat, Mercedes ^{[1
,2
]}

机构：

[1] Univ Barcelona, Fac Pharm & Food Sci, Lab Organ Chem, Barcelona 08028, Spain

[2] Univ Barcelona, Inst Biomed IBUB, Barcelona 08028, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 04期

关键词：

alkaloids; asymmetric synthesis; decahydroquinolines; lactams; total synthesis; FUSED OCTAHYDROQUINOLIZINE ALKALOIDS; DIPOLAR CYCLOADDITION CASCADE; ENANTIOSELECTIVE SYNTHESIS; SKELETON; CONSTRUCTION; CYCLIZATION; MYRIBERINE; UNITS;

D O I：

10.1002/adsc.202301062

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A dynamic kinetic asymmetric transformation, involving the generation of four stereogenic centers with a well-defined configuration, occurs in the cyclocondensation of diastereomeric mixtures of 2-oxocyclohexanepropionic acid racemates 6 with (1S,2R)-cis-aminoindanol: two major tetracyclic lactams, 7 a and 7 b, that differ in the configuration of the four stereocenters on the decahydroquinoline moiety were obtained. From the above lactams, the removal of the chiral auxiliary, the introduction of a 2-piperidone ring, and the closure of the diazine ring complete the first enantioselective total synthesis of the Myrioneuron alkaloid (-)-schoberine B and its enantiomer (+)-schoberine B.

引用

收藏

页码：948 / 954

页数：7

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