@article{29a2cbb0b9324a469a350dbe38e25261,
title = "Stereocontrolled total synthesis and biological evaluation of (-)- and (+)-petrosin and its derivatives",
abstract = "Total synthesis of (-)- and (+)-petrosin was accomplished. Stereocontrolled construction of the quinolizidine ring was achieved through a diastereoselective Mannich reaction and an aza-Michael reaction. Head-to-tail dimerization was performed by assembly of the two monomers using Suzuki-Miyaura cross coupling and subsequent ring-closing metathesis to construct the 16-membered ring. Biological evaluation of synthetic (-)- and (+)-petrosin and its derivatives indicated that the bispiperidine structure was necessary for the inhibition of syncytium formation.",
keywords = "Alkaloids, HIV, Macrocycle, Ring-closing metathesis, aza-Michael reaction",
author = "Hiroki Toya and Takahito Satoh and Kentaro Okano and Kiyosei Takasu and Masataka Ihara and Atsushi Takahashi and Haruo Tanaka and Hidetoshi Tokuyama",
note = "Funding Information: We thank Prof. Motomasa Kobayashi (Osaka Univ.) for providing spectral data of natural petrosin. This work was supported by the Cabinet Office, Government of Japan through its {\textquoteleft}Funding Program for Next Generation World-Leading Researchers ( LS008 ){\textquoteright} and by the JSPS , Japan, the KAKENHI , a Grant-in-Aid for Scientific Research (B) ( 20390003 ), a Grant-in-Aid for Scientific Research (A) ( 26253001 ), Platform for Drug Discovery, Informatics, and Structural Life Science, and the JSPS predoctoral fellowship to H.T. Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",
year = "2014",
month = oct,
day = "28",
doi = "10.1016/j.tet.2014.08.009",
language = "English",
volume = "70",
pages = "8129--8141",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "43",
}
