187040-04-6Relevant articles and documents
Sporolide B: Synthetic studies
Gladding, Jeffery A.,Bacci, James P.,Shaw, Scott A.,Smith III, Amos B.
, p. 6697 - 6706 (2011/10/01)
Studies directed toward the synthesis of the architecturally complex marine natural product sporolide B are described. Synthetic analysis suggested advanced hydroquinone and benzodiquinane fragments, which upon elaboration were successfully united via an
Process for producing ecteinascidin compounds
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, (2008/06/13)
The present invention is directed to a synthetic process for the formation of ecteinascidin compounds and related structures, such as the saframycins. In one particularly preferred embodiment, the present invention provides a synthetic route for the formation of ecteinascidin 743 (1), STR1 an exceedingly potent and rare marine-derived antitumor agent which is slated for clinical trials. The process of this invention is enantio- and stereocontrolled, convergent and short. Also disclosed are novel process intermediates, useful not only in the total synthesis of ecteinascidin 743, but also other known ecteinascidin compounds, including derivatives and analogs thereof.
Synthetic approaches toward ecteinascidins. Part 1. Preparation of an (E)-2-arylidene-3-benzyl-1,5-imino-3-benzazocin-4-one having a protected phenol in the E-ring
Saito, Naoki,Tashiro, Kyoichi,Maru, Yukie,Yamaguchi, Kentaro,Kubo, Akinori
, p. 53 - 70 (2007/10/03)
A synthetic strategy for the preparation of ecteinascidins isolated from the Caribbean tunicate Ecteinascidia turbinata and an efficient synthesis of a key tricyclic lactam intermediate 32 are described.The key step is the intramolecular cyclization of the allylic alcohol 15 to the (E)-1,5-imino-3-benzazocine 16.Cyclization of 15 (R = Me, Bn) afforded the desired product 16 in good yield.However, treatment of 15 (R = MOM) under acidic conditions gave compound 18 in high yield, the structure of which was determined by X-ray crystallography.Finally, 16 was converted into (E)-N-methyltricyclic lactam 32 that can serve as a synthetic precursor of ecteinascidins.