ENYNONES IN ORGANIC-SYNTHESIS .8. SYNTHESIS OF THE ANTIMICROBIAL-CYTOTOXIC AGENT JUNCUSOL AND MEMBERS OF THE EFFUSOL CLASS OF PHENOLS

被引：19

作者：

JACOBI, PA

KRAVITZ, JI

ZHENG, WJ

机构：

[1] Hall-Atwater Laboratories, Wesleyan University, Middletown

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 02期

关键词：

D O I：

10.1021/jo00107a017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new syntheses of phenols have been developed which have been utilized in an efficient preparation of the antimicrobial-cytotoxic agent juncusol (22) and several members of the effusol (23) class of phenols. These results complement our earlier studies with enynones of type 42 and provide for the highly efficient conversion of 42 to either methylenecyclopentenones 45 or phenols of type 47 or 54 with virtually 100% selectivity.

引用

页码：376 / 385

页数：10

共 49 条

[1] STRUCTURE OF EFFUSOL - NEW PHENOLIC CONSTITUENT FROM JUNCUS-EFFUSUS
BHATTACHARYYA, J
[J]. EXPERIENTIA, 1980, 36 (01): : 27 - 28
[2] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS
BLANCHETTE, MA
CHOY, W
DAVIS, JT
ESSENFELD, AP
MASAMUNE, S
ROUSH, WR
SAKAI, T
[J]. TETRAHEDRON LETTERS, 1984, 25 (21) : 2183 - 2186
[3] REGIOSPECIFIC TOTAL SYNTHESIS OF JUNCUSOL
BOGER, DL
MULLICAN, MD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) : 4045 - 4050
[4] PHENANTHRENE SYNTHESIS - THE SYNTHESIS OF EFFUSOL A 9,10-DIHYDROPHENANTHRENE FROM THE MARSH GRASS JUNCUS-EFFUSUS
CARVALHO, CF
SARGENT, MV
STANOJEVIC, E
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (10) : 2111 - 2117
[5] ANTI-MICROBIAL ACTIVITY OF JUNCUSOL, A NOVEL 9-10-DIHYDROPHENANTHRENE FROM THE MARSH PLANT JUNCUS-ROEMERIANUS
CHAPATWALA, KD
DELACRUZ, AA
MILES, DH
[J]. LIFE SCIENCES, 1981, 29 (19) : 1997 - 2001
[6] ENANTIOSPECIFIC TOTAL SYNTHESIS OF PSEUDOPTEROSIN-A AND PSEUDOPTEROSIN-E
COREY, EJ
CARPINO, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) : 5472 - 5474
[7] SYNTHESIS OF ALPHA,BETA-UNSATURATED ALDEHYDES
CRESP, TM
SARGENT, MV
VOGEL, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (01): : 37 - 41
[8] SYNTHESIS OF CYCLOPENTANECARBOXALDEHYDE - AN UNDERGRADUATE ORGANIC CHEMISTRY LABORATORY EXPERIMENT
DEV, V
[J]. JOURNAL OF CHEMICAL EDUCATION, 1970, 47 (06) : 476 - &
[9] THERMAL [1,7]-SIGMATROPIC HYDROGEN SHIFT VERSUS ELECTROCYCLIZATION OF DIENYLALLENE SULFOXIDES
ELNAGAR, HY
OKAMURA, WH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) : 3060 - 3066
[10] ANTICONVULSANTS - SPIROHYDANTOINS AND DERIVATIVES OF TETRAHYDRONAPHTHALENE
FAUST, JA
JULES, LH
YEE, L
SAHYUN, M
[J]. JOURNAL OF THE AMERICAN PHARMACEUTICAL ASSOCIATION, 1957, 46 (02): : 118 - 124

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