Three-component coupling via the squarate ester cascade as a concise route to the bioactive triquinane sesquiterpene hypnophilin

被引：46

作者：

Geng, F ^{[1
]}

Liu, J ^{[1
]}

Paquette, LA ^{[1
]}

机构：

[1] Ohio State Univ, Evans Chem Labs, Columbus, OH 43210 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 01期

关键词：

D O I：

10.1021/ol0102388

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A squarate ester cascade is used to provide in one step, via the coupling of three reactants, a highly oxygenated linear triquinane product. The latter is transformed in nine steps into hypnophilin. The access route involves a combination of chlorination, reduction, dehydration, and oxidation maneuvers In the proper sequence.

引用

页码：71 / 73

页数：3

共 27 条

[1] A SAMARIUM(II) IODIDE PROMOTED TANDEM RADICAL CYCLIZATION - THE TOTAL SYNTHESIS OF (+/-)-HYPNOPHILIN AND THE FORMAL SYNTHESIS OF (+/-)-CORIOLIN
FEVIG, TL
ELLIOTT, RL
CURRAN, DP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (15) : 5064 - 5067
[2] ANTIBIOTICS FROM BASIDIOMYCETES .24. ANTIBIOTICS WITH A REARRANGED HIRSUTANE SKELETON FROM PLEUROTELLUS-HYPNOPHILUS (AGARICALES)
GIANNETTI, BM
STEFFAN, B
STEGLICH, W
KUPKA, J
ANKE, T
[J]. TETRAHEDRON, 1986, 42 (13) : 3587 - 3593
[3] ANTIBIOTICS FROM BASIDIOMYCETES .14. ISOLATION AND BIOLOGICAL CHARACTERIZATION OF HYPNOPHILIN, PLEUROTELLOL, AND PLEUROTELLIC ACID FROM PLEUROTELLUS-HYPNOPHILUS (BERK) SACC
KUPKA, J
ANKE, T
GIANNETTI, BM
STEGLICH, W
[J]. ARCHIVES OF MICROBIOLOGY, 1981, 130 (03) : 223 - 227
[4] An efficient general synthesis of squarate esters
Liu, H
Tomooka, CS
Moore, HW
[J]. SYNTHETIC COMMUNICATIONS, 1997, 27 (12) : 2177 - 2180
[5] ACETYLIDE ANIONS EXERT COMPLETE CONTROL OVER ALDOLIZATION DURING THE DIRECT CONVERSION OF SQUARATE ESTERS INTO POLYQUINANES
MORWICK, T
DOYON, J
PAQUETTE, LA
[J]. TETRAHEDRON LETTERS, 1995, 36 (14) : 2369 - 2372
[6] Mapping the chemical reactivity of polyquinanes produced by 2-fold addition of vinyl anions to squarate esters. A bicyclic case study
Morwick, TM
Paquette, LA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) : 146 - 152
[7] DIRECT ELABORATION OF COMPLEX POLYQUINANES THROUGH 2-FOLD ADDITION OF VINYL ANIONS TO SQUARATE ESTERS
NEGRI, JT
MORWICK, T
DOYON, J
WILSON, PD
HICKEY, ER
PAQUETTE, LA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (25) : 12189 - 12190
[8] Generation and cycloaddition behavior of spirocyclic carbonyl ylides. Application to the synthesis of the pterosin family of sesquiterpenes
Padwa, A
Curtis, EA
Sandanayaka, VP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) : 73 - 81
[9] Paquette L. A., 1987, POLYQUINANE CHEM
[10] Paquette LA, 1998, EUR J ORG CHEM, V1998, P1709

← 1 2 3 →