The First Total Synthesis of Synparvolide C

被引：9

作者：

Sabitha, Gowravaram ^{[1
]}

Sandeep, AnkiReddy ^{[1
]}

Rao, Allu Senkara ^{[1
]}

Yadav, Jhillu S. ^{[1
]}

机构：

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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 29期

关键词：

Total synthesis; Natural products; Oxygen heterocycles; Lactones; Metathesis; Epoxidation; STEREOSELECTIVE TOTAL-SYNTHESIS; 5,6-DIHYDRO-ALPHA-PYRONES;

D O I：

10.1002/ejoc.201300913

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first stereoselective total synthesis of synparvolide C has been accomplished. An acid-catalyzed epoxide ring-opening reaction and ring-closing metathesis (RCM) were used for the cyclic ether and -lactone formation, respectively, to furnish the core structure of the target molecule. These reactions along with a succession of functional group manipulations led to the preparation of the natural product. The spectral and analytical data were used to establish the absolute configuration.

引用

页码：6702 / 6709

页数：8

共 22 条

[1]

[Anonymous], 1989, Progress In The Chemistry Of Organic Natural Products

[2]

Collett LA, 1998, PROG CH ORG NAT PROD, V75, P181

[3] 5,6-dihydro-alpha-pyrones from Syncolostemon paviflorus [J].

DaviesColeman, MT ;

Rivett, DEA .

PHYTOCHEMISTRY, 1996, 41 (04) :1085-1092

[4] Anti-staphylococcal and cytotoxic compounds from Hyptis pectinata [J].

Fragoso-Serrano, M ;

Gibbons, S ;

Pereda-Miranda, R .

PLANTA MEDICA, 2005, 71 (03) :278-280

[5]

Jose-Luis A., 2004, J ORG CHEM, V69, P7108

[6] Callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata [J].

Kobayashi, M ;

Higuchi, K ;

Murakami, N ;

Tajima, H ;

Aoki, S .

TETRAHEDRON LETTERS, 1997, 38 (16) :2859-2862

[7] Application of molecular mechanics in the total stereochemical elucidation of spicigerolide, a cytotoxic 6-tetraacetyl-oxyheptenyl-5,6-dihydro-α-pyrone from Hyptis spicigera [J].

Pereda-Miranda, R ;

Fragoso-Serrano, M ;

Cerda-García-Rojas, CM .

TETRAHEDRON, 2001, 57 (01) :47-53

[8]

PEREDAMIRANDA R, 1995, RECENT ADV PHYTOCHEM, V29, P83

[9] STRUCTURE AND STEREOCHEMISTRY OF PECTINOLIDES AC, NOVEL ANTIMICROBIAL AND CYTOTOXIC 5,6-DIHYDRO-ALPHA-PYRONES FROM HYPTIS-PECTINATA [J].

PEREDAMIRANDA, R ;

HERNANDEZ, L ;

VILLAVICENCIO, MJ ;

NOVELO, M ;

IBARRA, P ;

CHAI, HY ;

PEZZUTO, JM .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (04) :583-593

[10] Stereoselective total synthesis of (+)-(6R,2′S)-cryptocaryalactone and (-)-(6S,2′S)-epi cryptocaryalactone [J].

Sabitha, Gowravaram ;

Bhaskar, V. ;

Reddy, S. Siva Sankara ;

Yadav, J. S. .

TETRAHEDRON, 2008, 64 (44) :10207-10213

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