A CONCISE SYNTHESIS OF THE BRASSINOLIDE SIDE-CHAIN

被引：23

作者：

BACK, TG

BLAZECKA, PG

KRISHNA, MV

机构：

[1] Department of Chemistry, University of Calgary, Calgary

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 37期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4039(00)93468-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The brassinolide side chain was produced by the addition of (E)-propenyllithium to the C-22 aldehyde 2, followed by Sharpless epoxidation and epoxide opening with 1-Pr2CuCNLi2.

引用

页码：4817 / 4818

页数：2

共 15 条

[1] SYNTHESIS OF CASTASTERONE AND FORMAL SYNTHESIS OF BRASSINOLIDE FROM STIGMASTEROL VIA A SELENOSULFONATION APPROACH [J].

BACK, TG ;

KRISHNA, MV .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :454-457

[2] OXIDATION REACTIONS USING UREA HYDROGEN-PEROXIDE - A SAFE ALTERNATIVE TO ANHYDROUS HYDROGEN-PEROXIDE [J].

COOPER, MS ;

HEANEY, H ;

NEWBOLD, AJ ;

SANDERSON, WR .

SYNLETT, 1990, (09) :533-535

[3] STEREOSELECTIVE SYNTHESIS OF BRASSINOLIDE - A PLANT-GROWTH PROMOTING STEROIDAL LACTONE [J].

FUNG, S ;

SIDDALL, JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (21) :6580-6581

[4] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[5] BRASSINOLIDE, A PLANT GROWTH-PROMOTING STEROID ISOLATED FROM BRASSICA-NAPUS POLLEN [J].

GROVE, MD ;

SPENCER, GF ;

ROHWEDDER, WK ;

MANDAVA, N ;

WORLEY, JF ;

WARTHEN, JD ;

STEFFENS, GL ;

FLIPPENANDERSON, JL ;

COOK, JC .

NATURE, 1979, 281 (5728) :216-217

[6] TRANSITION-METAL-CATALYZED SILYLMETALLATION OF ACETYLENES AND ITS APPLICATION TO THE STEREOSELECTIVE SYNTHESIS OF STEROIDAL SIDE-CHAIN [J].

HAYAMI, H ;

SATO, M ;

KANEMOTO, S ;

MORIZAWA, Y ;

OSHIMA, K ;

NOZAKI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (13) :4491-4492

[7] AN IMPROVED SYNTHESIS OF PLANT-GROWTH REGULATING STEROID BRASSINOLIDE AND ITS CONGENERS [J].

KAMETANI, T ;

KATOH, T ;

FUJIO, J ;

NOGIWA, I ;

TSUBUKI, M ;

HONDA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) :1982-1991

[8] SUBSTITUTION-REACTIONS OF SECONDARY HALIDES AND EPOXIDES WITH HIGHER-ORDER, MIXED ORGANOCUPRATES, R2CU(CN)LI2 - SYNTHETIC, STEREOCHEMICAL, AND MECHANISTIC ASPECTS [J].

LIPSHUTZ, BH ;

WILHELM, RS ;

KOZLOWSKI, JA ;

PARKER, D .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :3928-3938

[9] BRASSINOLIDE AND ITS ANALOGS .5. SYNTHESIS OF NATURALLY-OCCURRING BRASSINOSTEROIDS EMPLOYING CLEAVAGE OF 23,34-EPOXIDES AS KEY REACTIONS - SYNTHESIS OF BRASSINOLIDE, CASTASTERONE, DOLICHOLIDE, DOLICHOSTERONE, HOMODOLICHOLIDE, HOMODOLICHOSTERONE, 6-DEOXOCASTASTERONE AND 6-DEOXODOLICHOSTERONE [J].

MORI, K ;

SAKAKIBARA, M ;

OKADA, K .

TETRAHEDRON, 1984, 40 (10) :1767-1781

[10]

REICH HJ, 1978, SYNTHESIS-STUTTGART, P299

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