The chemistry of .alpha.-silyl carbonyl compounds. 10. A two-step preparation of .alpha.-alkylidene .gamma.-lactones from .gamma.-lactones: a synthesis of (.+-.)-ancepsenolide

Larson, Gerald L.; Perez, R. M. Betancourt De

doi:10.1021/jo00225a052

Cited by 32 publications

(16 citation statements)

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“…226 Three total syntheses for ancepsenolide have been reported. [227][228][229] The latest synthesis, which proceeded in 31% overall yield in seven steps, established the absolute stereochemistry of ancepsenolide as 5S, 5'S. 229 Another dilactone, hydroxyancepsenolide (286), was later isolated from this same organism and its structure was identified by spectroscopic and chemical methods.…”

Section: A Pterogorgia (Xiphigorgia)anceps (Pallas)mentioning

confidence: 99%

The natural products chemistry of West Indian gorgonian octocorals

1995

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Plexauddae flourish as they do nowhere in the world. Gorgonian corals (order Gorgonacea, phylum Cnidaria) are 4571 4572 A.D. RODRIGUEZ conspicuous members of most tropical and subtropical marine habitats, being the most abundant octocorals found in the West Indies. With over 195 species documented from these two major families, gorgonian octocorals represent an estimated 38% of the known fauna, l Studies of the natural products chemistry of this interesting group of marine invertebrates began in the late 1950's. Since these early investigations, numerous studies of the chemistry of gorgonian corals have been published and summarized. 2-9 This Report documents the exciting chemistry that has been generated through the investigation of gorgonian octocorals from the West Indian region.It includes only research published in refereed journals up to December, 1994. A short communication in Science by Burkholder and Burkholder in 1958, highlighting the occurrence of antibiotic substances in gorgonian corals from Puerto Rico, was used as the starting point for the present review, to This Report is not intended to be comprehensive but instead concentrates on novel marine natural products with interesting biological and pharmaceutical properties. With the exception of several unusual sterols having interesting functionalities, marine sterols, carotenoids, fatty acids, and biopolymers isolated have not been included, since they have been reviewed by specialists, l 1-15 Studies of the chemical ecology aiming at the elucidation of the defensive roles of secondary metabolites from West Indian gorgonians and the value of secondary metabolite composition as a chemotaxonomic tool are discussed. The cited articles were retrieved from computer literature searches by use of Chemical Abstracts (CA Selects), MarinLit, STN International and also NAPRALERT. Terms such as West Indian, Caribbean, gorgonian, sea whip, octocoral, and phylla names were used. The primary focus will be the structural chemistry and biological activities of the metabolites produced by a relatively small group of gorgonians found within a limited geographic area. Wherever possible, every effort was made to record the biological and pharmacological properties of new metabolites. Since marine natural products in general are often the targets of synthetic chemists, we include synthetic work, where available, on novel compounds isolated from these animals.We hope to illustrate the diversity of compounds produced by West Indian gorgonians, while highlighting their specialized ability to biosynthesize secondary metabolites with promising pharmacological activity. 16-19 NATURAL PRODUCTS CHEMISTRYGorgonian metabolites possess novel structures that are largely unknown from terrestrial sources. These animals are now recognized to produce acetogenins, sesquiterpenoids, diterpenoids, prostanoids, and, in some cases, highly functionalized steroids. 7 The chemistry of West Indian gorgonian octocorals will be presented taxonomically according to genus and species (in alphabetic...

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Section: A Pterogorgia (Xiphigorgia)anceps (Pallas)mentioning

confidence: 99%

The natural products chemistry of West Indian gorgonian octocorals

1995

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“…The reaction of esters and γ-lactone enolates with diphenylmethylsilyl chloride is reported to be atypical and to give the C-silylated product (Scheme 11). 38 Enantioselective deprotonation by chiral lithium amide bases has been reported. The degree of asymmetric induction depends on the base and on the bulkiness of the alkyl group in the cyclohexanone (Scheme 12).…”

Section: Alkali Metal Enolates By Deprotonation Of Carbonyl Compoundsmentioning

confidence: 99%

2.06 Formation of Enolates

Mekelburger

Wilcox

2014

Comprehensive Organic Synthesis II

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“…Functionalized butenolides such as (−)-blastmycinolactol K, (+)-blastmycinone L, (−)-NFX-2 M and (+)-antimycinone N are polyketide metabolites and show antifungal and antitumor properties, while S and T are mosquito larvicides [41] (Figure 1). Many of these butenolides A-T have been synthesized by using a combination of various metal-mediated dry reactions such as LDA-mediated diastereoselective alkylation/methylation, reductive deamination, asymmetric dihydroxylation, lactonisation, elimination, hydrotelluration, carbonyl reduction, enzymatic resolution, Te/Li exchange followed by lactonisation, aldol condensation followed by β-elimination, DCC-mediated coupling, reductive dehydroxylation or Ru-catalyzed olefin-alkyne Alder ene reaction as key steps [42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60]. Herein, we planned to use simple organocatalytic reactions with a combination of other simple reactions in a one-pot manner in ambient conditions to produce the butenolides in high yields.…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic Enantiospecific Total Synthesis of Butenolides

2021

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Biologically important, chiral natural products of butenolides, (−)-blastmycinolactol, (+)-blastmycinone, (−)-NFX-2, (+)-antimycinone, lipid metabolites, (+)-ancepsenolide, (+)-homoancepsenolide, mosquito larvicidal butenolide and their analogues were synthesized in very good yields in a sequential one-pot manner by using an organocatalytic reductive coupling and palladium-mediated reductive deoxygenation or organocatalytic reductive coupling and silica-mediated reductive deamination as the key steps.

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The chemistry of .alpha.-silyl carbonyl compounds. 10. A two-step preparation of .alpha.-alkylidene .gamma.-lactones from .gamma.-lactones: a synthesis of (.+-.)-ancepsenolide

Cited by 32 publications

References 0 publications

The natural products chemistry of West Indian gorgonian octocorals

The natural products chemistry of West Indian gorgonian octocorals

2.06 Formation of Enolates

Organocatalytic Enantiospecific Total Synthesis of Butenolides

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