First Total Synthesis of Cryptopyranmoscatone A3 and Cryptopyranmoscatone B4

被引：4

作者：

Reddy, A. Maheswara ^{[1
]}

Sabitha, Gowravaram ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Nat Prod Chem Div, Hyderabad 500007, India

来源：

SYNOPEN | 2018年 / 2卷 / 01期

关键词：

oxa-Michael addition; Brown asymmetric allylation; ring-closing metathesis; cross metathesis;

D O I：

10.1055/s-0036-1591931

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of cryptopyranmoscatones A3 and B4 has been accomplished from D-ribose or but-3-ynol. The key steps involved in the synthesis are oxa-Michael addition, highly diastereoselective Brown allylation, and ring closing metathesis (RCM) and cross metathesis (CM) reactions.

引用

页码：58 / 63

页数：6

共 38 条

[1] Stereoselective syntheses of naturally occurring 5,6-dihydropyran-2-ones [J].

Alberto Marco, J. ;

Carda, Miguel ;

Murga, Juan ;

Falomir, Eva .

TETRAHEDRON, 2007, 63 (14) :2929-2958

[2] Efficient asymmetric synthesis of (+)-SCH 351448 [J].

Bolshakov, S ;

Leighton, JL .

ORGANIC LETTERS, 2005, 7 (17) :3809-3812

[3] CHIRAL SYNTHESIS VIA ORGANOBORANES .21. ALLYLBORATION AND CROTYLBORATION OF ALPHA-CHIRAL ALDEHYDES WITH DIISOPINOCAMPHEYLBORON AS THE CHIRAL AUXILIARY [J].

BROWN, HC ;

BHAT, KS ;

RANDAD, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1570-1576

[4] ASYMMETRIC CARBON CARBON BOND FORMATION VIA BETA-ALLYLDIISOPINOCAMPHEYLBORANE - SIMPLE SYNTHESIS OF SECONDARY HOMOALLYLIC ALCOHOLS WITH EXCELLENT ENANTIOMERIC PURITIES [J].

BROWN, HC ;

JADHAV, PK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) :2092-2093

[5]

Martins CVB, 2008, LETT DRUG DES DISCOV, V5, P74

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

Cavalheiro, AJ ;

Yoshida, M .

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

[7] Formal synthesis of (+)-SCH 351448: the Prins cyclization approach [J].

Chan, Kok-Ping ;

Ling, Yvonne Hui ;

Loh, Teck-Peng .

CHEMICAL COMMUNICATIONS, 2007, (09) :939-941

[8] Cytotoxic activity of (S)-goniothalamin and analogues against human cancer cells [J].

de Fátima, A ;

Kohn, LK ;

de Carvalho, JE ;

Pilli, RA .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (03) :622-631

[9] Absolute configurations of all four stereoisomers of cryptocaryalactone and deacetyl cryptocaryalactone [J].

Drewes, SE ;

Horn, MM ;

Ramesar, NS ;

Ferreira, D ;

Nel, RJJ ;

Hutchings, A .

PHYTOCHEMISTRY, 1998, 49 (06) :1683-1687

[10]

Drouet KE, 2000, CHEM-EUR J, V6, P1987, DOI 10.1002/1521-3765(20000602)6:11<1987::AID-CHEM1987>3.0.CO

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