SYNTHESIS OF VICINAL STEREOGENIC TERTIARY AND QUATERNARY CENTERS USING CHIRAL BICYCLIC LACTAMS AND DIASTEREOSELECTIVE PROTONATION - ASYMMETRIC-SYNTHESIS OF (+)-LAURENE

被引：21

作者：

SCHWARZ, JB ^{[1
]}

MEYERS, AI ^{[1
]}

机构：

[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 20期

关键词：

D O I：

10.1021/jo00125a042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral bicyclic lactam 5, previously reported in the synthesis of(-)-alpha-cuparenone, was used to construct the more complex title compound 2. A mixture of cyclopentenones 8 and 9 was subjected to deprotonation/reprotonation to provide 8 in high diastereomeric excess. Transformation of 8 to the title compound was achieved by catalytic hydrogenation to 13, followed by methylenation with the Tebbe reagent.

引用

页码：6511 / 6514

页数：4

共 16 条

[1] CHETTY GL, 1964, TETRAHEDRON LETT, P73
[2] ASYMMETRIC CONSTRUCTION OF QUATERNARY CARBONS FROM CHIRAL MALONATES - TOTAL SYNTHESES OF (+)-EPILAURENE AND (-)-ISOLAURENE
FADEL, A
CANET, JL
SALAUN, J
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (01) : 27 - 30
[3] CARBONYL METHYLENATION OF EASILY ENOLIZABLE KETONES
HIBINO, J
OKAZOE, T
TAKAI, K
NOZAKI, H
[J]. TETRAHEDRON LETTERS, 1985, 26 (45) : 5579 - 5580
[4] HIBINO J, 1985, TETRAHEDRON LETT, V26, P5581
[5] IRIE T, 1965, TETRAHEDRON LETT, P3619
[6] LAURENE A SESQUITERPENE HYDROCARBON FROM LAURENCIA SPECIES
IRIE, T
SUZUKI, T
YASUNARI, Y
KUROSAWA, E
MASAMUNE, T
[J]. TETRAHEDRON, 1969, 25 (02) : 459 - &
[7] KRAUSE N, 1994, ANGEW CHEM INT EDIT, V33, P1764, DOI 10.1002/anie.199417641
[8] Lombardo L, 1987, ORG SYNTH, V65, P81
[9] LANTHANIDES IN ORGANIC-CHEMISTRY .1. SELECTIVE 1,2 REDUCTIONS OF CONJUGATED KETONES
LUCHE, JL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (07) : 2226 - 2227
[10] KETONE METHYLENATION WITHOUT EPIMERIZATION - TOTAL SYNTHESIS OF (+/-) LAURENE
MCMURRY, JE
BEROLDIN.LA
[J]. TETRAHEDRON, 1974, 30 (14) : 2027 - 2032

← 1 2 →