A Stereoselective Total Synthesis of Verbalactone

被引：17

作者：

Das, Biswanath ^{[1
]}

Laxminarayana, Keetha ^{[1
]}

Krishnaiah, Martha ^{[1
]}

Kumar, Duddukuri Nandan ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

HELVETICA CHIMICA ACTA | 2009年 / 92卷 / 09期

关键词：

ENANTIOSELECTIVE SYNTHESIS; HOMOALLYLIC ALCOHOLS; VERBASCUM-UNDULATUM; MASSOIALACTONE; EXOPHILIN;

D O I：

10.1002/hlca.200900083

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereoselective total synthesis of verbalactone has been achieved starting from commercially available hexanal. The sequence involves Maruoka allylation, diastereoselective iodine-induced electrophillic cyclization, ring opening of epoxide, and Yamaguchi macrolactonization as the key steps.

引用

页码：1840 / 1844

页数：5

共 16 条

[1] A short and highly diastereoselective synthesis of verbalactone [J].

Allais, Florent ;

Louvel, Marie-Cecile ;

Cossy, Janine .

SYNLETT, 2007, (03) :451-452

[2] CARBONATE EXTENSION - A VERSATILE PROCEDURE FOR FUNCTIONALIZATION OF ACYCLIC HOMOALLYLIC ALCOHOLS WITH MODERATE STEREOCONTROL [J].

BARTLETT, PA ;

MEADOWS, JD ;

BROWN, EG ;

MORIMOTO, A ;

JERNSTEDT, KK .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (21) :4013-4018

[3] REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF EPOXY ALCOHOLS AND TRIOLS FROM ALLYLIC AND HOMOALLYLIC ALCOHOLS VIA IODO CARBONATES [J].

BONGINI, A ;

CARDILLO, G ;

ORENA, M ;

PORZI, G ;

SANDRI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (24) :4626-4633

[4] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[5] Exophilin A, a new antibiotic from a marine microorganism Exophiala pisciphila [J].

Doshida, J ;

Hasegawa, H ;

Onuki, H ;

Shimidzu, N .

JOURNAL OF ANTIBIOTICS, 1996, 49 (11) :1105-1109

[6] A highly stereoselective asymmetric synthesis of (-)-lobeline and (-)-sedamine [J].

Felpin, FX ;

Lebreton, J .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) :9192-9199

[7] First total synthesis of verbalactone, a macrocyclic dilactone isolated from Verbascum undulatum [J].

Gogoi, S ;

Barua, NC ;

Kalita, B .

TETRAHEDRON LETTERS, 2004, 45 (29) :5577-5579

[8] A practical enantioselective synthesis of massoialactone via hydrolytic kinetic resolution [J].

Gupta, P ;

Naidu, SV ;

Kumar, P .

TETRAHEDRON LETTERS, 2004, 45 (04) :849-851

[9] Bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide as a μ-oxo-type chiral Lewis acid:: Application to catalytic asymmetric allylation of aldehydes [J].

Hanawa, H ;

Hashimoto, T ;

Maruoka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) :1708-1709

[10] RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].

INANAGA, J ;

HIRATA, K ;

SAEKI, H ;

KATSUKI, T ;

YAMAGUCHI, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993

← 1 2 →