First total synthesis and determination of the absolute configuration of strictifolione, a new 6-(ω-phenylalkenyl)-5,6-dihydro-α-pyrone, isolated from Cryptocarya strictifolia

被引：27

作者：

Juliawaty, LD

Watanabe, Y

Kitajima, M

Achmad, SA

Takayama, H

Aimi, N

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

[2] Inst Teknol Bandung, Dept Chem, Bandung 40132, Indonesia

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 48期

关键词：

Crytocarya; alpha-pyrone; chiral total synthesis; absolute configuration;

D O I：

10.1016/S0040-4039(02)02181-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from (S)-malic acid and (S)-glycidol, the first total synthesis of strictifolione, a new 6-(omega-phenylalkenyl)-5,6-dihydro-alpha-pyrone isolated from Cryptocarya strictifolia, was accomplished, which confirmed its structure including the absolute configuration. of the asymmetric centers. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：8657 / 8660

页数：4

相关论文

共 25 条

[1] ENANTIOSELECTIVE SYNTHESIS OF THE METHYLENECYCLOPROPANE DERIVATIVE RELATED TO HYPOGLYCINE, FROM MALIC-ACID [J].

ACHMATOWICZ, B ;

KABAT, MM ;

KRAJEWSKI, J ;

WICHA, J .

TETRAHEDRON, 1992, 48 (46) :10201-10210

[2]

BLAKEMORE PR, 1988, SYNLETT, P26

[3] 6-[ω-arylalkenyl]-5,6-dihydro-α-pyrones from Cryptocarya moschata (Lauraceae) [J].

Cavalheiro, AJ ;

Yoshida, M .

PHYTOCHEMISTRY, 2000, 53 (07) :811-819

[4] Asymmetric total synthesis of callystatin A: Asymmetric aldol additions with titanium enolates of acyloxazolidinethiones [J].

Crimmins, MT ;

King, BW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :9084-9085

[5] Cryptocarya liebertiana and Ocotea bullata - Their phytochemical relationship [J].

Drewes, SE ;

Horn, MH ;

Mavi, S .

PHYTOCHEMISTRY, 1997, 44 (03) :437-440

[6] ALPHA-PYRONES AND THEIR DERIVATIVES FROM 2 CRYPTOCARYA SPECIES [J].

DREWES, SE ;

HORN, MM ;

SHAW, RS .

PHYTOCHEMISTRY, 1995, 40 (01) :321-323

[7] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].

EVANS, DA ;

CHAPMAN, KT ;

CARREIRA, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578

[8] C-13 NMR CHEMICAL-SHIFT CORRELATIONS IN 1,3-DIOL ACETONIDES - IMPLICATIONS FOR THE STEREOCHEMICAL ASSIGNMENT OF PROPIONATE-DERIVED POLYOLS [J].

EVANS, DA ;

RIEGER, DL ;

GAGE, JR .

TETRAHEDRON LETTERS, 1990, 31 (49) :7099-7100

[9] THE DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING ME4NHB(OAC)3 [J].

EVANS, DA ;

CHAPMAN, KT .

TETRAHEDRON LETTERS, 1986, 27 (49) :5939-5942

[10]

FU X, 1993, PHYTOCHEMISTRY, V33, P1272, DOI 10.1016/0031-9422(93)85065-Y