Synthesis of (−)-TAN-2483A. Revision of the Structures and Syntheses of (±)-FD-211 (Waol A) and (±)-FD-212 (Waol B)

Abstract

[structure: see text] The structure of waol A has been revised from 1 to 6, the vinylogue of TAN-2483 A (5). Aldol reaction of 10b(c) with 2,4-hexadienal (11) affords 9b(c), which is subjected to iodoetherification with bis(sym-collidine)IPF(6) to provide 8b(c). Treatment with Et(3)N in CH(2)Cl(2) completes three-step syntheses of TAN-2483A (5) and waol A (6).

Chemical Constituents of the Fermented Broth of the Ascomycete Theissenia cinerea 89091602

“…The relative configurations of the HÀC(2), HÀC(3), HÀC (7), and HÀC(8) of 4 were determined as b, a, a, and b, respectively, as deduced by the key correlations HÀC(9)/ HÀC(8), HÀC(8)/HÀC (2), and HÀC(10)/HÀC(3) in the NOESY of 4. Although the diastereoisomers of 3 and 4, TAN-2483 A and B, have also been synthesized [6], this is the first report to describe them from a natural source with different configurations.…”

Waol A, trans-dihydrowaol A, and cis-dihydrowaol A: polyketide-derived γ-lactones from a Volutella species

“…First isolated in 1995 from a fermentation of Myceliophthora lutea TF-0409, 13 the structure of 1 was revised in 2003. 14,15 …”

Biologically active metabolites from the marine isolate of the fungus Myceliophthora lutea

“…In continuation of the search for producers of biologically active compounds among marine isolates of microscopic fungi, we determined that the fungus Myceliophthora lutea Costantin [4], which was isolated from marine sediments of Sakhalin Bay (Sea of Okhotsk), synthesizes compounds with antibacterial and cytotoxic activities. Little is known about secondary metabolites from fungi of the genus Myceliophthora although these fungi are often encountered and can be isolated from various substrates [5][6][7][8]. Herein we present data on the isolation and identification of known acremine A (2) [9] and previously unknown compounds called by us isoacremine D (1) and spiroacremines A (3) and B (4).…”