ASYMMETRIC-SYNTHESIS OF A PHEROMONE FOR ANDRENA-HAEMORRHOA F FROM A CHIRAL NITRO ALCOHOL OBTAINED BY THE YEAST REDUCTION OF A NITRO KETONE

被引：29

作者：

NAKAMURA, K

KITAYAMA, T

INOUE, Y

OHNO, A

机构：

[1] Institute for Chemical Research, Kyoto University, Uji, Kyoto

来源：

TETRAHEDRON | 1990年 / 46卷 / 21期

关键词：

D O I：

10.1016/S0040-4020(01)89061-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The α-position to the nitro group in 4-nitro-2-butanol or 5-nitro-2-pentanol was acylated under DBU-catalysis after the hydroxy group was protected by a t-butyl dimethylsilyl group. The present method has been applied to the asymmetric stereoselective synthesis of a pheromone for Andrena haemorrhoa F, which has an interesting spiroacetal strucure. © 1990.

引用

收藏

页码：7471 / 7481

页数：11

相关论文

共 9 条

[1] ALPHA-NITRO KETONES AND ESTERS FROM ACYLIMIDAZOLES [J].

CRUMBIE, RL ;

NIMITZ, JS ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (21) :4040-4045

[2]

FRANCKE W, 1981, Z NATURFORSCH C, V36, P928

[3]

MORI K, 1984, LIEBIGS ANN CHEM, P157

[4] STEREOCHEMICAL CONTROL IN MICROBIAL REDUCTION .12. (S)-4-NITRO-2-BUTANOL AS A SOURCE TO SYNTHESIZE NATURAL-PRODUCTS [J].

NAKAMURA, K ;

KITAYAMA, T ;

INOUE, Y ;

OHNO, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (01) :91-96

[5] ASYMMETRIC REDUCTION OF BETA-NITRO AND GAMMA-NITRO KETONES BY BAKERS-YEAST [J].

NAKAMURA, K ;

INOUE, Y ;

SHIBAHARA, J ;

OKA, S ;

OHNO, A .

TETRAHEDRON LETTERS, 1988, 29 (37) :4769-4770

[6] A NEW METHOD FOR REGIOSELECTIVE ALPHA-MONO-DEUTERATION OR ALPHA,ALPHA-DI-DEUTERATION OF CARBONYL-COMPOUNDS [J].

ONO, N ;

HAMAMOTO, I ;

MIYAKE, H ;

KAJI, A .

CHEMISTRY LETTERS, 1982, (07) :1079-1080

[7] NUCLEOPHILIC-SUBSTITUTION REACTION IN A NON-POLAR SOLVENT .4. ALKYLATION AND ACYLATION OF ACTIVE METHYLENE-COMPOUNDS USING 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE AS A BASE [J].

ONO, N ;

YOSHIMURA, T ;

SAITO, T ;

TAMURA, R ;

TANIKAGA, R ;

KAJI, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (06) :1716-1719

[8] A NEW SYNTHETIC METHOD - DIRECT REPLACEMENT OF THE NITRO-GROUP BY HYDROGEN OR DEUTERIUM [J].

ONO, N ;

MIYAKE, H ;

TAMURA, R ;

KAJI, A .

TETRAHEDRON LETTERS, 1981, 22 (18) :1705-1708

[9] A FREE-RADICAL CHAIN-REACTION INVOLVING ELECTRON-TRANSFER - THE REPLACEMENT OF THE NITRO-GROUP BY HYDROGEN USING TRIALKYLTIN HYDRIDE, A VARIATION OF THE KORNBLUM REACTION [J].

TANNER, DD ;

BLACKBURN, EV ;

DIAZ, GE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (06) :1557-1559