Intramolecular Wittig reaction:: A new synthesis of (S)-pyrrolam A

被引：14

作者：

Majik, Mahesh S. ^{[1
]}

Parameswaran, Perunninakulath S. ^{[2
]}

Tilve, Santosh G. ^{[1
]}

机构：

[1] Goa Univ, Dept Chem, Taleigao Plateau 403206, Goa, India

[2] CSIR, Chem Oceanog Div, Natl Inst Oceanog, Dona Paula Goa 403004, India

来源：

HELVETICA CHIMICA ACTA | 2008年 / 91卷 / 08期

关键词：

D O I：

10.1002/hlca.200890163

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A straightforward synthesis of (S)-pyrrolam A is described. The synthesis involves in situ generation of the phosphorane 3. followed by an intramolecular Wittig reaction to furnish (S)-pyrrolam A.

引用

页码：1500 / 1504

页数：5

共 28 条

[1] New access to indolizidine and pyrrolizidine alkaloids from an enantiopure proline:: Total syntheses of (-)-lentiginosine and (1R,2R,7aR)-Dihydroxypyrrolizidine [J].

Angle, Steven R. ;

Bensa, David ;

Belanger, Dominique S. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (15) :5592-5597

[2] First total synthesis of pyrrolam A [J].

Aoyagi, Y ;

Manabe, T ;

Ohta, A ;

Kurihara, T ;

Pang, GL ;

Yuhara, T .

TETRAHEDRON, 1996, 52 (03) :869-876

[3]

Arisawa M, 1997, SYNLETT, P1179

[4]

Arisawa M, 2000, CHEM PHARM BULL, V48, P1593

[5] Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].

Asano, N ;

Nash, RJ ;

Molyneux, RJ ;

Fleet, GWJ .

TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680

[6] Dess-Martin periodinane oxidation of alcohols in the presence of stabilized phosphorus ylides: A convenient method for the homologation of alcohols via unstable aldehydes [J].

Barrett, AGM ;

Hamprecht, D ;

Ohkubo, M .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9376-9378

[7] Manganese dioxide can oxidise unactivated alcohols under in situ oxidation-Wittig conditions [J].

Blackburn, L ;

Wei, XD ;

Taylor, RJK .

CHEMICAL COMMUNICATIONS, 1999, (14) :1337-1338

[8]

Crich D, 1999, SYNLETT, P67

[9] Convenient in situ synthesis of nonracemic N-protected β-amino aldehydes from β-amino acids.: Applications in Wittig reactions and heterocycle synthesis [J].

Davies, SB ;

McKervey, MA .

TETRAHEDRON LETTERS, 1999, 40 (06) :1229-1232

[10] ASYMMETRIC SYNTHESIS VIA METALATED CHIRAL HYDRAZONES - ENANTIOSELECTIVE ALKYLATION OF CYCLIC-KETONES AND ALDEHYDES [J].

ENDERS, D ;

EICHENAUER, H .

CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (08) :2933-2960

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