Journal ArticleDOI
Synthesis of macrocyclic terpenoids by intramolecular cyclization VII. Total synthesis of (±)-cubitene
TLDR
In this article, a stereoselective total synthesis of (±)-cubitene, a diterpene isolated from termite soldiers, and its stereisomer has been achieved utilizing the anion-induced intramolecular cyclization.About:
This article is published in Tetrahedron Letters.The article was published on 1982-01-01. It has received 19 citations till now. The article focuses on the topics: Total synthesis & Terpene.read more
Citations
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Journal ArticleDOI
Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products
TL;DR: This review highlights 21st century terpene total syntheses which themselves use small, ter pene-derived materials as building blocks and an outlook to the future of research in this area is highlighted.
Journal ArticleDOI
An Adventurous Synthetic Journey with MNBA from Its Reaction Chemistry to the Total Synthesis of Natural Products
TL;DR: In this paper, a novel cyclization reaction of ω-hydroxycarboxylic acids (seco-acids) using 4-trifluoromethylbenzoic anhydride (TFBA) and Lewis acid catalysts was established.
Book ChapterDOI
Cembranoids, Pseudopteranoids, and Cubitanoids of Natural Occurrence
I. Wahlberg,A.-M. Eklund +1 more
TL;DR: The structures of (+)-cembrene (1), a macrocyclic diterpene hydrocarbon isolated from pine oleoresins (1, 2), and of the two epimeric cembratrienediols 35 and 36, which were obtained from tobacco (3), were reported in 1962.
Journal ArticleDOI
Synthesis of A-B-C-ring segment of thyrsiferol construction of a strained tetrahydropyran ring existent as a boat form
Masaru Hashimoto,Toshiyuki Kan,Mitsutoshi Yanagiya,Haruhisa Shirahama,Takeshi Matsumoto,Takeshi Matsumoto +5 more
TL;DR: Tricyclic bromoether 17, which contained twenty of thirty carbons of thyrsiferol (1d ), was synthesized in optically active form starting from trivial compounds 2 and 3.
Journal ArticleDOI
Total Synthesis of 2‐Hydroxytetracosanolide and 2‐Hydroxy‐24‐oxooctacosanolide By Using an Effective Lactonization
TL;DR: The key cyclization to produce the 25- or 29-membered lactone core is performed by using 2-methyl-6-nitrobenzoic anhydride (MNBA) with a stoichiometric amount of 4-(dimethylamino)pyridine (DMAP) or a catalytic amount of 2- methyl- 6-nitropyridine N-oxide ( DMAPO).
References
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Journal ArticleDOI
Cubitene: an irregular twelve-membered-ring diterpene from a termite soldier
Glenn D. Prestwich,Glenn D. Prestwich,Glenn D. Prestwich,David F. Wiemer,Jerrold Meinwald,Jon Clardy,Jon Clardy +6 more
TL;DR: Cubitene was isolated from the hexane extract of C umbratus soldier heads by chromatography over Florisil followed by preparative GLC High resolution mass spectroscopy indicated the formula of cubitene to be C/sub 20/H/sub 32/ as mentioned in this paper.
Journal ArticleDOI
Synthesis of macrocyclic terpenoids by intramolecular cyclization VI. Synthesis of 3Z-cembrene A and cembrenene
TL;DR: Two 14-membered diterpenes, 3Z-cembrene A and cembrenene, isolated from a termite and a soft coral, respectively, were synthesized by the anion-induced cyclization of geranylgeranyl phenyl sulfide as mentioned in this paper.