bipinnatin-j and intricarene

bipinnatin-j has been researched along with intricarene* in 2 studies

Other Studies

2 other study(ies) available for bipinnatin-j and intricarene

Article	Year
Total synthesis of (+)-intricarene using a biogenetically patterned pathway from (-)-bipinnatin J, involving a novel transannular [5+2] (1,3-dipolar) cycloaddition. Organic & biomolecular chemistry, 2009, Nov-07, Volume: 7, Issue:21 An asymmetric synthesis of the furanobutenolide-based macrocyclic diterpene (-)-bipinnatin J (4a) isolated from the gorgonian octocoral Pseudopterogorgonia bipinnata is described. The synthesis is based on elaboration of the chiral lactone-substituted vinyl iodide 26b from (+)-glycidol, followed by an intermolecular Stille coupling reaction with the stannylfurfural 27, leading to 28a, and then an intramolecular Nozaki-Hiyama-Kishi allylation reaction, 28b --> 4a. Treatment of (-)-bipinnatin J (4a) with VO(acac)2-tBuO2H followed by acetylation of the tautomeric hydroxypyranone product 7/8, next gave the acetoxypyrone 30. When the acetoxypyranone 30 was heated in acetonitrile in the presence of DBU, it gave (+)-intricarene 1, which is found in P. kallos, via a novel transannular [5+2] (or 1,3-dipolar) cycloaddition involving the butenolide-oxidopyrylium ion intermediate 31. We believe that this total synthesis of (+)-intricarene 1 mimics its most likely origin in nature via oxidation of (-)-bipinnatin J (4a), presumably involving photochemically generated singlet oxygen or possibly a P450 monooxygenase enzyme system. Topics: Biomimetics; Diterpenes; Stereoisomerism; Triterpenes	2009
Exploring biosynthetic relationships among furanocembranoids: synthesis of (-)-bipinnatin J, (+)-intricarene, (+)-rubifolide, and (+)-isoepilophodione B. Organic letters, 2006, Dec-07, Volume: 8, Issue:25 The asymmetric total synthesis of (-)-bipinnatin J and its conversion into (+)-intricarene through a transannular 1,3-dipolar cycloaddition is described. In addition, the conversion of (-)-bipinnatin J into (+)-rubifolide and (+)-isoepilophodione B is reported. Biosynthetic relationships among furanocembranoids and the possible role of 1,3-dipolar cycloadditions in biosynthesis are discussed. [reaction: see text] Topics: Cyclization; Diterpenes; Magnetic Resonance Spectroscopy; Oxidation-Reduction; Stereoisomerism; Triterpenes	2006

Article

Year

Total synthesis of (+)-intricarene using a biogenetically patterned pathway from (-)-bipinnatin J, involving a novel transannular [5+2] (1,3-dipolar) cycloaddition.

Organic & biomolecular chemistry, 2009, Nov-07, Volume: 7, Issue:21

An asymmetric synthesis of the furanobutenolide-based macrocyclic diterpene (-)-bipinnatin J (4a) isolated from the gorgonian octocoral Pseudopterogorgonia bipinnata is described. The synthesis is based on elaboration of the chiral lactone-substituted vinyl iodide 26b from (+)-glycidol, followed by an intermolecular Stille coupling reaction with the stannylfurfural 27, leading to 28a, and then an intramolecular Nozaki-Hiyama-Kishi allylation reaction, 28b --> 4a. Treatment of (-)-bipinnatin J (4a) with VO(acac)2-tBuO2H followed by acetylation of the tautomeric hydroxypyranone product 7/8, next gave the acetoxypyrone 30. When the acetoxypyranone 30 was heated in acetonitrile in the presence of DBU, it gave (+)-intricarene 1, which is found in P. kallos, via a novel transannular [5+2] (or 1,3-dipolar) cycloaddition involving the butenolide-oxidopyrylium ion intermediate 31. We believe that this total synthesis of (+)-intricarene 1 mimics its most likely origin in nature via oxidation of (-)-bipinnatin J (4a), presumably involving photochemically generated singlet oxygen or possibly a P450 monooxygenase enzyme system.

Topics: Biomimetics; Diterpenes; Stereoisomerism; Triterpenes

2009

Exploring biosynthetic relationships among furanocembranoids: synthesis of (-)-bipinnatin J, (+)-intricarene, (+)-rubifolide, and (+)-isoepilophodione B.

Organic letters, 2006, Dec-07, Volume: 8, Issue:25

The asymmetric total synthesis of (-)-bipinnatin J and its conversion into (+)-intricarene through a transannular 1,3-dipolar cycloaddition is described. In addition, the conversion of (-)-bipinnatin J into (+)-rubifolide and (+)-isoepilophodione B is reported. Biosynthetic relationships among furanocembranoids and the possible role of 1,3-dipolar cycloadditions in biosynthesis are discussed. [reaction: see text]

Topics: Cyclization; Diterpenes; Magnetic Resonance Spectroscopy; Oxidation-Reduction; Stereoisomerism; Triterpenes

2006