Enantioselective synthesis of α-methyl-D-cysteine and lanthionine building blocks via α-methyl-D-serine-β-lactone

被引:62
作者
Smith, ND [1 ]
Goodman, M [1 ]
机构
[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
关键词
D O I
10.1021/ol034025p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] We report here the enantioselective synthesis of Boc-alpha-methyl-D-cysteine(PMB)-OH and lanthionine building blocks through the regloselective ring opening of key intermediate Boc-alpha-methyl-D-serine-beta-lactone.
引用
收藏
页码:1035 / 1037
页数:3
相关论文
共 16 条
[1]   SYNTHESIS OF OPTICALLY PURE ALPHA-AMINO-ACIDS VIA SALTS OF ALPHA-AMINO-BETA-PROPIOLACTONE [J].
ARNOLD, LD ;
MAY, RG ;
VEDERAS, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2237-2241
[2]   CONVERSION OF SERINE BETA-LACTONES TO CHIRAL ALPHA-AMINO-ACIDS BY COPPER-CONTAINING ORGANOLITHIUM AND ORGANOMAGNESIUM REAGENTS [J].
ARNOLD, LD ;
DROVER, JCG ;
VEDERAS, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) :4649-4659
[3]   CONVERSION OF SERINE TO STEREOCHEMICALLY PURE BETA-SUBSTITUTED ALPHA-AMINO-ACIDS VIA BETA-LACTONES [J].
ARNOLD, LD ;
KALANTAR, TH ;
VEDERAS, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7105-7109
[4]   Enantioselective synthesis of (S)- and (R)-α-methylserines:: application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals [J].
Avenoza, A ;
Cativiela, C ;
Corzana, F ;
Peregrina, JM ;
Sucunza, D ;
Zurbano, MM .
TETRAHEDRON-ASYMMETRY, 2001, 12 (06) :949-957
[5]   ASYMMETRIC DIHYDROXYLATION (AD) OF N,N-DIALKYL AND N-METHOXY-N-METHYL ALPHA,BETA-UNSATURATED AND BETA,GAMMA-UNSATURATED AMIDES [J].
BENNANI, YL ;
SHARPLESS, KB .
TETRAHEDRON LETTERS, 1993, 34 (13) :2079-2082
[6]   ASYMMETRIC-SYNTHESIS OF ALPHA-ALKYL-ALPHA-AMINO ACIDS FROM CHROMIUM CARBENE-COMPLEX-DERIVED BETA-LACTAMS [J].
COLSON, PJ ;
HEGEDUS, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :5918-5924
[7]   TOTAL SYNTHESIS OF (-)-TANTAZOLE-B [J].
FUKUYAMA, T ;
XU, LH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8449-8450
[8]   ASYMMETRIC ALDOL REACTION OF ALPHA-ISOCYANOCARBOXYLATES WITH PARAFORMALDEHYDE CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEXES - CATALYTIC ASYMMETRIC-SYNTHESIS OF ALPHA-ALKYLSERINES [J].
ITO, Y ;
SAWAMURA, M ;
SHIRAKAWA, E ;
HAYASHIZAKI, K ;
HAYASHI, T .
TETRAHEDRON LETTERS, 1988, 29 (02) :235-238
[9]   STUDIES ON 2-AZIRIDINECARBOXYLIC ACID .9. CONVENIENT SYNTHESIS OF OPTICALLY-ACTIVE S-ALKYLCYSTEINE, THREO-S-ALKYL-BETA-METHYLCYSTEINE, AND LANTHIONINE DERIVATIVES VIA THE RING-OPENING REACTION OF AZIRIDINE BY SEVERAL THIOLS [J].
NAKAJIMA, K ;
ODA, H ;
OKAWA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (02) :520-522
[10]   SN2 ring opening of β-lactones:: An alternative to catalytic asymmetric conjugate additions [J].
Nelson, SG ;
Wan, ZH ;
Stan, MA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4680-4683