73991-91-0Relevant articles and documents
Aplysillamides A and B, new antimicrobial guanidine alkaloids from the Okinawan marine sponge Psammaplysilla purea
Honma, Kaori,Tsuda, Masashi,Mikami, Yuzuru,Kobayashi, Junichi
, p. 3745 - 3748 (1995)
Two new guanidine alkaloids, aplysillamides A (1) and B (2), with antimicrobial activity have been isolated from the Okinawan marine sponge Psammaplysilla purea and the structures elucidated on the basis of spectroscopic data. The absolute stereochemistry
The first stereoselective total synthesis of lankanolide. Part 2
Hamada, Tatsuo,Kobayashi, Yukinari
, p. 4347 - 4350 (2007/10/03)
The seco-acid derivative designed by conformation calculation and lactonization experiment of model seco-acids was synthesized, and subjected to macrolactonization to afford the lactone derivative. The lankanolide was synthesized via several steps after the lactonization, and the synthetic lankanolide was confirmed to have the same physical data (NMR, mass, IR and αD) as the lankanolide prepared from lankamycin according to the reported method.
Applications of crotyldiisopinocampheylboranes in synthesis: A formal total synthesis of (+)-calyculin A
Anderson, Oren P.,Barrett, Anthony G.M.,Edmunds, Jeremy J.,Hachiya, Shun-Ichiro,Hendrix, James A.,Horita, Kiyoshi,Malecha, James W.,Parkinson, Christopher J.,Vansickle, Andrew
, p. 1562 - 1592 (2007/10/03)
The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth-Meyers approach to the synthesis of the oxazole fragment.
Synthesis of a diastereoisomer of the C-15-C-26 segment of amphidinolide L
Tsuda, Masashi,Hatakeyama, Akiko,Kobayashi, Jun'ichi
, p. 149 - 155 (2007/10/03)
In order to determine the absolute stereochemistry of amphidinolide L 1, a cytotoxic macrolide from a marine dinoflagellate, (16R, 18S, 20R, 22S, 23R, and 25R)-2, one of the eight possible diastereoisomers of the C(15)-C(26) segment has been synthesized,
Amphidinolides: Unique macrolides from marine dinoflagellates
Ishibashi, Masami,Kobayashi, Jun'ichi
, p. 543 - 572 (2007/10/03)
A series of macrolides, named amphidinolides, have been isolated from the laboratory-cultured marine dinoflagellates Amphidinium sp., which were symbionts of the Okinawan marine flatworm Amphiscolops sp. These macrolides possess unique chemical structures as well as cytotoxic activities. Here we describe our recent results on the isolation, structure elucidation, and biosynthesis of these unique macrolides.
Stereocontrolled Synthesis of Calyculin A: Construction of the C(15)-C(25) Spiroketal Unit
Barrett, Anthony G. M.,Edmunds, Jeremy J.,Horita, Kiyoshi,Parkinson, Christopher J.
, p. 1236 - 1238 (2007/10/02)
Two concise enantioselective syntheses of the C(15)-C(25) spiroketal unit of calyculin A, using derivatives of allyldiisopinocampheylborane efficiently to control 1,2- and 1,3-diol stereochemistries, are reported.