135708-75-7Relevant academic research and scientific papers
Total Synthesis and Stereochemical Revision of Stereocalpin A: Mirror-Image Approach for Stereochemical Assignments of the Peptide-Polyketide Macrocycle
Kaneda, Masato,Inuki, Shinsuke,Ohno, Hiroaki,Oishi, Shinya
, p. 3047 - 3060 (2018/03/25)
Stereocalpin A is a cyclic depsipeptide with cytotoxic activity isolated from the Antarctic lichen Stereocaulon alpinum. Although a number of synthetic investigations of the unprecedented 12-membered macrocycle of stereocalpin A with a dipeptide segment and a polyketide substructure have been conducted, the configurational assignment has not been completed. In this study, we achieved the first total synthesis and stereochemical revision of stereocalpin A. To facilitate the comprehensive assessment of eight possible stereocalpin A isomers, four stereoisomers of polyketide precursors were conjugated with l-Phe-l-MePhe and d-Phe-d-MePhe dipeptides (MePhe: N-methylphenylalanine) to provide four possible isomers and four mirror-image structures of the remaining isomers, respectively. The comparative NMR analysis of a series of stereoisomers revealed that stereocalpin A possesses 2R,4S,5R-configurations, which is unique among the related 12-membered hybrid peptide-polyketide natural products reported recently. The NOE correlations in the polyketide substructure of stereocalpin A were also retrospectively analyzed among the eight possible stereoisomers.
Total synthesis of the potent microtubule-stabilizing agent (+)-discodermolide
Harried, Scott S.,Lee, Christopher P.,Yang,Lee, Tony I. H.,Myles, David C.
, p. 6646 - 6660 (2007/10/03)
The total synthesis of the potent microtubule-stabilizing, antimitotic agent (+)-discodermolide is described. The convergent synthetic strategy takes advantage of the diastereoselective alkylation of a ketone enolate to establish the key C15-C16 bond. The synthesis is amenable to preparation of gram-scale quantities of (+)-discodermolide and analogues.
Synthetic studies toward ansatrienines: Application of the Evans- Tishchenko reaction to chiral enones
Schoening, Kai-Uwe,Hayashi,Powell, Douglas R.,Kirschning, Andreas
, p. 817 - 820 (2007/10/03)
Practical syntheses of the C9-C14 sterotriade 5 and the C1-C8 polyene unit 6 in ansatrienine A (mycotriene) (1a), and other ansamycin antibiotics is described. A key step for controlling the configuration of the stereogenic center at C13 involves the stereoselective reduction of enone 10 using the Evans-Tishchenko reaction.
Synthetic Studies toward Rapamycin: A Solution to a Problem in Chirality Merger through Use of the Ireland Reaction
Fisher, Matthew J.,Myers, Cheryl D.,Joglar, Jesus,Chen, Shu-Hui,Danishefsky, Samuel J.
, p. 5826 - 5834 (2007/10/02)
A program directed toward a total synthesis of rapamycin is described.This paper reports the synthesis of enoate 36, a fragment that would correspond to carbons 28-49 of rapamycin.The two building blocks required to reach 36 were allylic alcohol 5 and aci
