Total synthesis of (±)-hedychilactone B:: Stepwise allenoate diene cycloaddition to prepare trimethyldecalin systems

被引：26

作者：

Jung, Michael E. ^{[1
]}

Murakami, Masayuki ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 03期

关键词：

D O I：

10.1021/ol062811z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the diterpene hedychilactone B 1 is reported. The exo adduct 4x, the major product of the stepwise [4+2] cycloaddition of the diene 2 and the allenoate 3, has been converted into 1 via 7 steps, among them a key nonconjugative hydrolysis of a gamma-methylene silyl enol ether and an E-selective olefination.

引用

页码：461 / 463

页数：3

共 17 条

[1] AN INTRAMOLECULAR COBALT CYCLIZATION FOR THE CONSTRUCTION OF SUBSTITUTED PYRROLIDINES [J].

BALDWIN, JE ;

MOLONEY, MG ;

PARSONS, AF .

TETRAHEDRON, 1992, 48 (42) :9373-9384

[2] AN IMPROVED PREPARATION OF VINYL IODIDES [J].

BARTON, DHR ;

BASHIARDES, G ;

FOURREY, JL .

TETRAHEDRON LETTERS, 1983, 24 (15) :1605-1608

[3] SYNTHESIS OF COMPETENT NUCLEOPHILES FOR DELIVERING THE A RING OF TAXOL [J].

DIGRANDI, MJ ;

JUNG, DK ;

KROL, WJ ;

DANISHEFSKY, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4989-4992

[4] Synthesis of chiral organotin reagents:: synthesis of enantiomerically enriched bicyclo[2.2.1]hept-2-yl tin hydrides from camphor.: X-Ray crystal structures of (dimethyl)[(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]tin chloride and methyl(phenyl)bis[(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]stannane [J].

Helliwell, M ;

Thomas, EJ ;

Townsend, LA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (10) :1286-1296

[5] Versatile diastereoselectivity in formal [3,3]-sigmatropic shifts of substituted 1-alkenyl-3-alkylidenecyclobutanols and their silyl ethers [J].

Jung, ME ;

Nishimura, N ;

Novack, AR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11206-11207

[6]

JUNG ME, 1978, SYNTHESIS-STUTTGART, P588

[7] Total synthesis of (+/-)-hedychenone: Trimethyldecalin terpene systems via stepwise allenoate diene cycloaddition [J].

Jung, Michael E. ;

Murakami, Masayuki .

ORGANIC LETTERS, 2006, 8 (25) :5857-5859

[8] Synthetic approach to analogues of betulinic acid [J].

Jung, Michael E. ;

Duclos, Brian A. .

TETRAHEDRON, 2006, 62 (40) :9321-9334

[9] Enantioselective total synthesis and structure revision of spirodihydrobenzofuranlactam 1. Total synthesis of stachybotrylactam [J].

Kende, AS ;

Deng, WP ;

Zhong, M ;

Guo, XC .

ORGANIC LETTERS, 2003, 5 (10) :1785-1788

[10] THE CHEMISTRY OF ALPHA-SILYL CARBONYL-COMPOUNDS .10. A 2-STEP PREPARATION OF ALPHA-ALKYLIDENE GAMMA-LACTONES FROM GAMMA-LACTONES - A SYNTHESIS OF (+/-)-ANCEPSENOLIDE [J].

LARSON, GL ;

DEPEREZ, RMB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5257-5260

← 1 2 →