A short synthetic route towards merosesquiterpenes with a benzoxanthene skeleton

被引：21

作者：

Fernandez, Antonio ^{[1
]}

Alvarez, Esteban ^{[1
]}

Alvarez-Manzaneda, Ramon ^{[2
]}

Chahboun, Rachid ^{[1
]}

Alvarez-Manzaneda, Enrique ^{[1
]}

机构：

[1] Univ Granada, Fac Ciencias, Inst Biotecnol, Dept Quim Organ, E-18071 Granada, Spain

[2] Univ Almeria, Dept Quim & Fis, Area Quim Organ, Almeria 04120, Spain

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 86期

关键词：

PUUPEHENONE-RELATED METABOLITES; ENANTIOSPECIFIC SYNTHESIS; SPONGE; 8-EPIPUUPEHEDIONE; (+/-)-GAMMA-RUBROMYCIN; FUNCTIONALIZATION; (+)-PUUPEHENONE; HONGOQUERCINS; (-)-SCLAREOL; ANTIBIOTICS;

D O I：

10.1039/c4cc05116e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A short synthetic sequence for the preparation of merosesquiterpenes with a benzoxanthene skeleton starting from commercial (-)-sclareol is reported. The D ring of the target compound is obtained through a Diels-Alder cycloaddition, involving a dienoldiether derived from a tricyclic alpha, beta-enone synthesized in two steps from the starting diterpene. Utilizing this procedure, the preparation of (+)-hongoquercin A and the first synthesis of (+)-cyclospongiaquinone-1 were achieved.

引用

页码：13100 / 13102

页数：3

共 30 条

[1] Hongoquercins, new antibacterial agents from the fungus LL-23G227: Fermentation and biological activity [J].

Abbanat, DA ;

Singh, MP ;

Greenstein, M .

JOURNAL OF ANTIBIOTICS, 1998, 51 (08) :708-714

[2] Synthesis of decalin type chiral synthons based on enzymatic functionalisation and their application to the synthesis of (-)-ambrox and (+)-zonarol [J].

Akita, H ;

Nozawa, M ;

Shimizu, H .

TETRAHEDRON-ASYMMETRY, 1998, 9 (10) :1789-1799

[3] Diels-Alder cycloaddition approach to puupehenone-related metabolites: Synthesis of the potent angiogenesis inhibitor 8-epipuupehedione [J].

Alvarez-Manzaneda, E. J. ;

Chahboun, R. ;

Cabrera, E. ;

Alvarez, E. ;

Haidour, A. ;

Ramos, J. M. ;

Alvarez-Manzaneda, R. ;

Hmamouchi, M. ;

Bouanou, H. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (09) :3332-3339

[4] O3/Pb(OAc)4:: a new and efficient system for the oxidative cleavage of allyl alcohols [J].

Alvarez-Manzaneda, E. J. ;

Chahboun, R. ;

Cano, M. J. ;

Cabrera Torres, E. ;

Alvarez, E. ;

Alvarez-Manzaneda, R. ;

Haidour, A. ;

Ramos Lopez, J. M. .

TETRAHEDRON LETTERS, 2006, 47 (37) :6619-6622

[5] First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol [J].

Alvarez-Manzaneda, EJ ;

Chahboun, R ;

Pérez, IB ;

Cabrera, E ;

Alvarez, E ;

Alvarez-Manzaneda, R .

ORGANIC LETTERS, 2005, 7 (08) :1477-1480

[6] First enantiospecific synthesis of marine sesquiterpene quinol akaol A [J].

Alvarez-Manzaneda, Enrique ;

Chahboun, Rachid ;

Alvarez, Esteban ;

Fernandez, Antonio ;

Alvarez-Manzaneda, Ramon ;

Haidour, Ali ;

Miguel Ramos, Jose ;

Akhaouzan, Ali .

CHEMICAL COMMUNICATIONS, 2012, 48 (04) :606-608

[7] Total synthesis of both enantiomers of 15-oxopuupehenol methylenedioxy derivatives [J].

Arjona, O ;

Garranzo, M ;

Mahugo, J ;

Maroto, E ;

Plumet, J ;

Saez, B .

TETRAHEDRON LETTERS, 1997, 38 (41) :7249-7252

[8] An efficient stereoselective synthesis of cytotoxic 8-epipuupehedione [J].

Armstrong, V ;

Barrero, AF ;

Alvarez-Manzaneda, EJ ;

Cortés, M ;

Sepúlveda, B .

JOURNAL OF NATURAL PRODUCTS, 2003, 66 (10) :1382-1383

[9] Synthesis and antitumor activity of puupehedione and related compounds [J].

Barrero, AF ;

Alvarez-Manzaneda, EJ ;

Chahboun, R ;

Cortés, M ;

Armstrong, V .

TETRAHEDRON, 1999, 55 (52) :15181-15208

[10] Enantiospecific synthesis of (+)-puupehenone from (-)-sclareol and protocatechualdehyde [J].

Barrero, AF ;

AlvarezManzaneda, EJ ;

Chahboun, R .

TETRAHEDRON LETTERS, 1997, 38 (13) :2325-2328

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