Total Synthesis of (-)-Sacidumlignans B and D

被引：24

作者：

Rout, Jeetendra Kumar ^{[1
]}

Ramana, C. V. ^{[1
]}

机构：

[1] Natl Chem Lab CSIR NCL, Pune 411008, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 03期

关键词：

IODOXYBENZOIC ACID IBX; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ALCOHOLS; CLEAVAGE; MAGNOSHININ; REDUCTION; REAGENT; DECOMPOSITION; DERIVATIVES;

D O I：

10.1021/jo2021696

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of naturally occurring sacidumlignans A (1), B (2), and D (4) was executed and the absolute configuration of 2 and 4 was determined. A diastereoselective alpha- methylation of a lactone was used as the key step for the control of the chiral centers of the central lignan core. An acid mediated dehydrative cyclization of an aldehyde to construct the dihydronaphthalene unit of 2 and the aromatization of the intermediate dihydronaphthalene derivative to synthesize 1 are the key reactions employed in this regard.

引用

页码：1566 / 1571

页数：6

共 35 条

[1] Adlington M.G., 1976, TETRAHEDRON LETT, V34, P2955
[2] An Access to Chiral β-Benzyl-γ-butyrolactones and Its Application to the Synthesis of Enantiopure (+)-Secoisolariciresinol, (-)-Secoisolariciresinol, and (-)-Enterolactone
Allais, Florent
Pla, Thomas J. L.
Ducrot, Paul-Henri
[J]. SYNTHESIS-STUTTGART, 2011, (09): : 1456 - 1464
[3] A short asymmetric synthesis of (+)-lyoniresinol dimethyl ether
Assoumatine, T
Datta, PK
Hooper, TS
Yvon, BL
Charlton, JL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (12) : 4140 - 4144
[4] Balogh V., 1971, J ORG CHEM, V36, P1339
[5] Enantioselective Total Synthesis of (-)-Kibdelone C
Butler, John R.
Wang, Chao
Bian, Jianwei
Ready, Joseph M.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (26) : 9956 - 9959
[6] ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES
EVANS, DA
ENNIS, MD
MATHRE, DJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) : 1737 - 1739
[7] A MILD OXIDIZING REAGENT FOR ALCOHOLS AND 1,2-DIOLS - O-IODOXYBENZOIC ACID (IBX) IN DMSO
FRIGERIO, M
SANTAGOSTINO, M
[J]. TETRAHEDRON LETTERS, 1994, 35 (43) : 8019 - 8022
[8] OXIDATION OF ALCOHOLS WITH O-IODOXYBENZOIC ACID (IBX) IN DMSO - A NEW INSIGHT INTO AN OLD HYPERVALENT IODINE REAGENT
FRIGERIO, M
SANTAGOSTINO, M
SPUTORE, S
PALMISANO, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) : 7272 - 7276
[9] REDUCTION OF ALDEHYDES AND KETONES TO ALCOHOLS AND HYDROCARBONS THROUGH USE OF ORGANOSILANE-BORON TRIFLUORIDE SYSTEM
FRY, JL
ORFANOPOULOS, M
ADLINGTON, MG
DITTMAN, WR
SILVERMAN, SB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02) : 374 - 375
[10] Lignans and their degraded derivatives from Sarcostemma acidum
Gan, LS
Yang, SP
Fan, CQ
Yue, JM
[J]. JOURNAL OF NATURAL PRODUCTS, 2005, 68 (02): : 221 - 225

← 1 2 3 4 →