A NOVEL ENANTIOSELECTIVE SYNTHESIS OF (+)-BIOTIN

被引：15

作者：

DEROOSE, FD ^{[1
]}

DECLERCQ, PJ ^{[1
]}

机构：

[1] STATE UNIV GHENT,DEPT ORGAN CHEM,ORGAN SYNTH LAB,KRIJGSLAAN 281 S4,B-9000 GHENT,BELGIUM

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(00)79354-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A conceptually simple enantioselective 14-step synthesis of (+)-biotin from L-cysteine is reported based upon an intramolecular 1,3-dipolar cycloaddition sequence involving (i) elimination of bromide 8 to the endocyclic thioenol ether 9, (ii) thermolysis of the ene carbamoyl azide 9 to the exocyclic thioenol ether 10. Both the synthesis of 8 and the final transformation of 10 into (+)-biotin are based upon literature precedents.

引用

页码：4365 / 4368

页数：4

共 33 条

[1] A SYNTHESIS OF BIOTIN BASED ON CYCLOADDITION OF A THIOCARBONYL YLIDE [J].

ALCAZAR, V ;

TAPIA, I ;

MORAN, JR .

TETRAHEDRON, 1990, 46 (03) :1057-1062

[2]

[Anonymous], 1963, COMP BIOCHEM, V11, P66

[3]

Aoki Y., 1975, Method for Synthesis of Optically Active Lactones, Patent No. [3,876,656, 3876656]

[4] SYNTHESIS OF D-BIOTIN FROM L-CYSTINE VIA INTRAMOLECULAR [3+2] CYCLOADDITION [J].

BAGGIOLINI, EG ;

LEE, HL ;

PIZZOLATO, G ;

USKOKOVIC, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (23) :6460-6462

[5] PREPARATION OF (3A-ALPHA,6A-ALPHA)-1,3-DIBENZYLHEXAHYDRO-1H-THIENO[3,4-D]-IMIDAZOL-2(3H)-ONE - A KEY BIOTIN INTERMEDIATE [J].

BATES, HA ;

SMILOWITZ, L ;

LIN, J .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (06) :899-901

[6] SYNTHESIS OF (+)-BIOTIN - EFFICIENT RESOLUTION OF KEY INTERMEDIATES [J].

BIHOVSKY, R ;

BODEPUDI, V .

TETRAHEDRON, 1990, 46 (23) :7667-7676

[7]

CASUTT M, Patent No. 3926690

[8] RING CLOSURES FROM ENECARBAMOYL AZIDES - SYNTHESES OF TETRAHYDRO-3-INDAZOLINONES AND 4-IMIDAZOLIN-2-ONES [J].

CHUPP, JP .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1971, 8 (04) :557-&

[9] STEREOSPECIFIC TOTAL SYNTHESIS OF D-BIOTIN FROM L-(+)-CYSTEINE [J].

CONFALONE, PN ;

PIZZOLATO, G ;

BAGGIOLINI, EG ;

LOLLAR, D ;

USKOKOVIC, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (20) :5936-5938

[10] STEREOSPECIFIC TOTAL SYNTHESIS OF D-BIOTIN FROM L(+)-CYSTEINE [J].

CONFALONE, PN ;

PIZZOLATO, G ;

BAGGIOLINI, EG ;

LOLLAR, D ;

USKOKOVIC, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (21) :7020-7026

← 1 2 3 4 →