850656-74-5Relevant academic research and scientific papers
Total synthesis of the proposed structure of brevenal
Fuwa, Haruhiko,Ebine, Makoto,Sasaki, Makoto
, p. 9648 - 9650 (2007/10/03)
Total synthesis of the proposed structure of brevenal, a natural marine polycyclic ether product, has been accomplished. The synthesis features (i) convergent synthesis of the pentacyclic polyether skeleton using our developed Suzuki-Miyaura coupling stra
Total synthesis, structure revision, and absolute configuration of (-)-brevenal
Fuwa, Haruhiko,Ebine, Makoto,Bourdelais, Andrea J.,Baden, Daniel G.,Sasaki, Makoto
, p. 16989 - 16999 (2007/10/03)
Total synthesis of structure 1 originally proposed for brevenal, a nontoxic polycyclic ether natural product isolated from the Florida red tide dinoflagellate, Karenia brevis, was accomplished. The key features of the synthesis involved (i) convergent ass
Convergent total synthesis of gymnocin-A and evaluation of synthetic analogues
Tsukano, Chihiro,Ebine, Makoto,Sasaki, Makoto
, p. 4326 - 4335 (2007/10/03)
The first total synthesis of gymnocin-A (1), a cytotoxic polycyclic ether isolated from a notorious red tide dinoflagellate, Karenia mikimotoi, has been accomplished. The synthesis relies heavily on the Suzuki-Miyaura cross-coupling-based methodology to assemble the tetradecacyclic polyether skeleton. Convergent union of the GHI (5) and KLMN (6) rings, both of which were prepared from a common intermediate 7, and the subsequent ring closure of the J ring delivered the GHIJKLMN ring. The crucial coupling between the ABCD and FGHIJKLMN ring fragments (3 and 4, respectively) and stereoselective installation of the C17 hydroxyl group, followed by cyclization of the E ring gave rise to the tetradecacyclic polyether skeleton 2. Finally, incorporation of the 2-methyl-2-butenal side chain completed the total synthesis of gymnocin-A. The convergent nature of the synthesis, which employs three fragments of comparable complexity, is well-suited for preparation of various structural analogues of gymnocin-A to explore the structure-activity relationship. The results of preliminary structure-activity relationship studies of several synthetic analogues are also provided.
