Stereoselective construction of the key intermediate for the synthesis of the tetrahydropyranyl antifungal agents (+)-restricticin and (+)-lanomycin

被引：6

作者：

Honda, T ^{[1
]}

Satoh, A ^{[1
]}

Yamada, T ^{[1
]}

Hayakawa, T ^{[1
]}

Kanai, K ^{[1
]}

机构：

[1] Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 142, Japan

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 03期

关键词：

D O I：

10.1039/a707534k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective construction of the key intermediate for the synthesis of naturally occurring antifungal agents, such as (+)-restricticin and (+)-lanomycin, has been achieved by employing a chelation-controlled aldol reaction of methyl alpha-methyltetronate with (R)-cyclohexylideneglyceraldehyde as a key step.

引用

页码：397 / 405

页数：9

共 15 条

[1]

CHIDA N, 1996, CARBOHYDR LETT, V2, P47

[2] STRUCTURE ELUCIDATION OF RESTRICTICIN, A NOVEL ANTIFUNGAL AGENT FROM PENICILLIUM-RESTRICTUM [J].

HENSENS, OD ;

WICHMANN, CF ;

LIESCH, JM ;

VANMIDDLESWORTH, FL ;

WILSON, KE ;

SCHWARTZ, RE .

TETRAHEDRON, 1991, 47 (24) :3915-3924

[3] STEREOCONTROLLED SYNTHESIS OF THE B-RING MOIETY OF SESBANIMIDE ALKALOIDS - FORMAL CHIRAL SYNTHESIS OF SESBANIMIDE-A AND SESBANIMIDE-B [J].

HONDA, T ;

YAMADA, T ;

HAYAKAWA, T ;

KANAI, K .

TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :247-254

[4] CHELATION CONTROL IN THE ALDOL REACTION OF TETRONIC ACID - APPLICATION TO THE SYNTHESIS OF PENTOSES, ARABITOL AND RIBITOL [J].

HONDA, T ;

HAYAKAWA, T ;

KONDOH, H ;

OKUYAMA, A ;

TSUBUKI, M .

CHEMISTRY LETTERS, 1991, (10) :1861-1864

[5] CHELATION CONTROLLED ALDOL REACTION OF TETRONIC ACID DIANION WITH KETONES [J].

HONDA, T ;

KONDOH, H ;

OKUYAMA, A ;

HAYAKAWA, T ;

TSUBUKI, M ;

NAGASE, H .

HETEROCYCLES, 1992, 33 (01) :67-72

[6] TOTAL SYNTHESIS OF RESTRICTICIN [J].

JENDRZEJEWSKI, S ;

ERMANN, P .

TETRAHEDRON LETTERS, 1993, 34 (04) :615-618

[7] ONE-STEP STEREOCHEMICAL DETERMINATION OF CONTIGUOUS 4 ACYCLIC CHIRAL CENTERS ON THE STEROIDAL SIDE-CHAIN - A NOVEL SYNTHESIS OF BRASSINOLIDE [J].

KAMETANI, T ;

KATOH, T ;

TSUBUKI, M ;

HONDA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7055-7060

[8] 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

[9]

Kang SH, 1996, SYNLETT, P515

[10] A NEW SERIES OF NATURAL ANTIFUNGALS THAT INHIBIT P450 LANOSTEROL C-14 DEMETHYLASE .1. TAXONOMY, FERMENTATION, ISOLATION AND STRUCTURAL ELUCIDATION [J].

MATSUKUMA, S ;

OHTSUKA, T ;

KOTAKI, H ;

SHIRAI, H ;

SANO, T ;

WATANABE, K ;

NAKAYAMA, N ;

ITEZONO, Y ;

FUJIU, M ;

SHIMMA, N ;

YOKOSE, K ;

OKUDA, T .

JOURNAL OF ANTIBIOTICS, 1992, 45 (02) :151-159

← 1 2 →