[3,3]SIGMATROPIC RING EXPANSION OF CYCLIC THIONOCARBONATES .12. SYNTHESIS OF (-)-YELLOW SCALE PHEROMONE

被引：12

作者：

HARUSAWA, S ^{[1
]}

TAKEMURA, S ^{[1
]}

YONEDA, R ^{[1
]}

KURIHARA, T ^{[1
]}

机构：

[1] OSAKA UNIV PHARMACEUT SCI,2-10-65 KAWAI,MATSUBARA,OSAKA 580,JAPAN

来源：

TETRAHEDRON | 1993年 / 49卷 / 46期

关键词：

D O I：

10.1016/S0040-4020(01)81549-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)-Yellow scale pheromone 1 has been synthesized by the route via [3,3]sigmatropic ring expansion of the 8-membered thionocarbonate 3 containing a diene moiety. The key Z-10-membered intermediate 2 was exclusively synthesized by a one-pot conversion from a chiral aldehyde (+)-4 and a dienyliodide 14.

引用

页码：10577 / 10586

页数：10

共 17 条

[1] SYNTHESES WITH SULFONES .49. STEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF (S)-(-)-3,9-DIMETHYL 6-(1-METHYLETHYL) (E)-5,8-DECADIEN-1-OL ACETATE, SEXUAL PHEROMONE OF YELLOW SCALE
ALVAREZ, E
CUVIGNY, T
DUPENHOAT, CH
JULIA, M
[J]. TETRAHEDRON, 1988, 44 (01) : 119 - 126
[2] SYNTHESIS OF (E)-3,9-DIMETHYL-6-ISOPROPYL-5,8-DECADIEN-1-YL ACETATE, THE SEX-PHEROMONE OF THE YELLOW SCALE AONIDIELLA-CITRINA (COQUILLETT) (HOMOPTERA, DIASPIDIDAE)
ANDERSON, RJ
HENRICK, CA
[J]. JOURNAL OF CHEMICAL ECOLOGY, 1979, 5 (05) : 773 - 779
[3] STEREOSELECTIVE SYNTHESIS OF THE AONIDIELLA-CITRINA SEX PHEROMONE (3S,5E)-(-)-3,9-DIMETHYL-6-ISOPROPYLDECA-5,8-DIEN-1-YL ACETATE
BAUDOUY, R
SANCHO, MR
[J]. TETRAHEDRON, 1991, 47 (48) : 10015 - 10022
[4] IDENTIFICATION OF THE SEX-PHEROMONE OF THE YELLOW SCALE AONIDIELLA-CITRINA(COQUILLETT)(HOMOPTERA, DIASPIDIDAE)
GIESELMANN, MJ
MORENO, DS
FARGERLUND, J
TASHIRO, H
ROELOFS, WL
[J]. JOURNAL OF CHEMICAL ECOLOGY, 1979, 5 (01) : 27 - 33
[5] [3,3]SIGMATROPIC RING EXPANSION OF CYCLIC THIONOCARBONATES .9. TOTAL SYNTHESIS OF (+/-)-YELLOW SCALE PHEROMONE VIA 10-MEMBERED THIOLCARBONATE
HARUSAWA, S
TAKEMURA, S
OSAKI, H
YONEDA, R
KURIHARA, T
[J]. TETRAHEDRON, 1993, 49 (35) : 7657 - 7666
[6] [3,3]SIGMATROPIC RING EXPANSION OF CYCLIC THIONOCARBONATES .8. HIGHLY STEREOSELECTIVE SYNTHESIS OF (Z)-DOUBLE BONDS OR (E)-DOUBLE BONDS BY CONTROLLING CHAIR-LIKE-BOAT-LIKE TRANSITION-STATES IN THE [3,3]SIGMATROPIC REARRANGEMENT OF 8-MEMBERED THIONOCARBONATES
HARUSAWA, S
OSAKI, H
FUJII, H
YONEDA, R
KURIHARA, T
[J]. TETRAHEDRON, 1992, 48 (43) : 9433 - 9450
[7] HARUSAWA S, UNPUB TETRAHEDRON LE
[8] JOHNSON WT, 1988, INSECTS FEED TREES S, P378
[9] PHEROMONE SYNTHESIS .48. STEREOSELECTIVE SYNTHESIS OF (S,E)-6-ISOPROPYL-3,9-DIMETHYL-5,8-DECADIENYL ACETATE, THE (S)-ENANTIOMER OF THE YELLOW SCALE PHEROMONE
MASUDA, S
KUWAHARA, S
SUGURO, T
MORI, K
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1981, 45 (11): : 2515 - 2520
[10] APPLICATION OF SILYLCUPRATION OF ALKYNES TO STEREOSPECIFIC AND REGIOSPECIFIC FORMATION OF TRISUBSTITUTED ALKENES - A SHORT SYNTHESIS OF YELLOW SCALE PHEROMONE
MILLAR, JG
[J]. TETRAHEDRON LETTERS, 1989, 30 (37) : 4913 - 4914

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