ENANTIOSELECTIVE SYNTHESIS OF NAGILACTONE-F VIA VINYLSILANE-TERMINATED CATIONIC CYCLIZATION

被引：30

作者：

BURKE, SD

KORT, ME

STRICKLAND, SMS

ORGAN, HM

SILKS, LA

机构：

[1] Department of Chemistry, University of Wisconsin-Madison, Madison

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 10期

关键词：

VINYLSILANE-MEDIATED CATIONIC CYCLIZATION; DITERPENOID SYNTHESIS; REMOTE FUNCTIONALIZATION; BARTON REACTION;

D O I：

10.1016/S0040-4039(00)76743-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective total synthesis of nagilactone F is described. Functionalized tricyclic intermediate 3 was prepared using a high-yielding acetal-initiated/vinylsilane-terminated polyene cyclization of 5. Intramolecular alkoxy radical-mediated remote functionalization established the D-ring of the nagilactone system.

引用

页码：1503 / 1506

页数：4

共 33 条

[1] STUDIES ON THE SYNTHESES OF SESQUITERPENE LACTONES .10. IMPROVED SYNTHESES OF (+)-TUBERIFERIN AND THE RELATED ALPHA-METHYLENE GAMMA-LACTONES AND THEIR BIOLOGICAL-ACTIVITIES
ANDO, M
WADA, T
KUSAKA, H
TAKASE, K
HIRATA, N
YANAGI, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) : 4792 - 4796
[2] RHODIUM-CATALYZED ISOMERIZATION OF SOME UNSATURATED ORGANIC SUBSTRATES
ANDRIEUX, J
BARTON, DHR
PATIN, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (04): : 359 - 363
[3] BARTON DHR, 1968, PURE APPL CHEM, V16, P1
[4] SYNTHESIS OF (+)-FRAGOLIDE AND (-)-PERENIPORIN-B VIA VINYLSILANE TERMINATED CATIONIC CYCLIZATION
BURKE, SD
SHANKARAN, K
HELBER, MJ
[J]. TETRAHEDRON LETTERS, 1991, 32 (36) : 4655 - 4658
[5] ENANTIOSELECTIVE SYNTHESIS OF THE NAGILACTONE RING-SYSTEM VIA VINYLSILANE-MEDIATED POLYENE CYCLIZATION
BURKE, SD
STRICKLAND, SMS
ORGAN, HM
SILKS, LA
[J]. TETRAHEDRON LETTERS, 1989, 30 (46) : 6303 - 6306
[6] SILICON-SUBSTITUTED DIENES IN THE INTRAMOLECULAR DIELS-ALDER REACTION - NAGILACTONE MODEL STUDIES
BURKE, SD
STRICKLAND, SMS
POWNER, TH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (04) : 454 - 459
[7] REMOTE FUNCTIONALIZATION AND MOLECULAR MODELING - OBSERVATIONS RELEVANT TO THE BARTON AND HYPOIODITE REACTIONS
BURKE, SD
SILKS, LA
STRICKLAND, SMS
[J]. TETRAHEDRON LETTERS, 1988, 29 (23) : 2761 - 2764
[8] SYNTHESIS OF (+)-DIHYDROCOMPACTIN AND (+)-COMPACTIN VIA VINYLSILANE TERMINATED CATIONIC CYCLIZATION
BURKE, SD
DEATON, DN
[J]. TETRAHEDRON LETTERS, 1991, 32 (36) : 4651 - 4654
[9] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS
CARLSEN, PHJ
KATSUKI, T
MARTIN, VS
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) : 3936 - 3938
[10] REVISED STRUCTURE OF PODOLACTONE-C, THE ANTILEUKEMIC COMPONENT OF PODOCARPUS-MILANJIANUS RENDLE
CASSADY, JM
LIGHTNER, TK
MCCLOUD, TG
HEMBREE, JA
BYRN, SR
CHANG, CJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (05) : 942 - 945

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