RADICAL-TYPE CYCLIZATION OF DIENES .6. SUBSTRATE-CONTROLLED ASYMMETRIC-SYNTHESIS OF (3AS,6AR)-(+)-3,3A,6,6A-TETRAHYDRO-2H-CYCLOPENTA[B]FURAN-2-ONE

被引：0
|
作者：
WEINGES, K
SCHWARZ, G
机构：
来源：
LIEBIGS ANNALEN DER CHEMIE | 1993年 / 07期
关键词：
CYCLOPENTA[B]FURAN-2-ONE, (3AS,6AR)-(+)-3,3A,6,6A-TETRAHYDRO-2H-; RADICALS; CYCLIZATION; CARVONE;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(R)-(-)-Carvone (1) was converted via straightforward reactions into 10-hydroxycarvone (4) which was cyclized to 5 via the mercury-mediated free-radical method. Periodate cleavage of 5 yields the bicyclic dione 6. Regio- and stereoselective reduction of 6 with lithium tri(tert-butyloxy)hydridoaluminate results in 7 (80% yield). 7 was directly converted into gamma-lactone 8 via Baeyer-Villiger oxidation. Saponification of 8 to 9, mesylation of 9 to 10 followed by elimination of methanesulfonic acid yield enantiomerically pure (3aS,6aR)-(+)-3,3a,6,6a-Tetrahydro-2H-cyclopenta[b]furan-2-one (11). The synthesis can be carried out with readily available, and economical, (S)-(+)-carvone to yield ent-11.
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页码：811 / 814
页数：4
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