332837-94-2Relevant academic research and scientific papers
An approach to the total synthesis of lankacidins: Synthesis of advanced macrocyclic precursors
Chen, Anqi,Nelson, Adam,Tanikkul, Nongluk,Thomas, Eric J.
, p. 1251 - 1254 (2001)
The macrocyclic tetraenes 11 and 19, possible precursors of lankacidin C 1, have been prepared using intramolecular Stille reactions to close the macrocyclic rings. The Stille precursor 10 was prepared by stereoselective acylation of the azetidinone 3 using the thioester 7. After reduction and deprotection, cyclisation gave the macrocyclic product 11 in 55% yield. Alternatively, the Boc-protected amino-ester 17 was prepared by ring-opening of the azetidinone, and cyclised to the macrocycle 19 in 48% yield.
Synthesis of macrocyclic precursors of lankacidins using Stille reactions of 4-(2-iodo-alkenyl)azetidinones and related compounds for ring closure
Brain, Christopher T.,Chen, Anqi,Nelson, Adam,Tanikkul, Nongluk,Thomas, Eric J.
experimental part, p. 6613 - 6625 (2010/10/19)
In the context of a proposed total synthesis of lankacidins, the synthesis of 4-(2-iodo-alkenyl)azetidinones and their participation in Stille coupling reactions have been investigated. 1-tert-Butyldimethylsilyl-4-(2-iodoethenyl) azetidinone was found to
Concise syntheses of (+)-macrosphelides A and B: Studies on the macro-ring closure strategy
Paek, Seung-Mann,Yun, Hwayoung,Kim, Nam-Jung,Jung, Jong-Wha,Chang, Dong-Jo,Lee, Sujin,Yoo, Jakyung,Park, Hyun-Ju,Suh, Young-Ger
supporting information; experimental part, p. 554 - 561 (2009/07/25)
Highly concise syntheses of (+)-macrosphelides A and B were accomplished in this study. The key feature of our synthetic route involved the direct three-carbon homologation of the readily available Weinreb amide 6 by the addition of a trans-vinylogous est
