Synthesis 2012; 44(15): 2340-2346
DOI: 10.1055/s-0031-1289813
paper
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of d-lyxo-Phytosphingosine and Formal Synthesis of Pachastrissamine via a Chiral 1,3-Oxazine

Yu Mu
a  School of Pharmacy, Sungkyunkwan University, Suwon 440-746, Republic of Korea
,
Ji-Yeon Kim
a  School of Pharmacy, Sungkyunkwan University, Suwon 440-746, Republic of Korea
,
Xiangdan Jin
a  School of Pharmacy, Sungkyunkwan University, Suwon 440-746, Republic of Korea
,
Seok-Hwi Park
a  School of Pharmacy, Sungkyunkwan University, Suwon 440-746, Republic of Korea
,
Jae-Eun Joo
b  Yonsung Fine Chemicals Co., Ltd., 129-9 Suchon-ri, Jangan-myeon, Hwaseong-si, Gyeonggi-do 445-944, Republic of Korea, Fax: +82(31)2928800   Email: whham@skku.edu
,
Won-Hun Ham*
a  School of Pharmacy, Sungkyunkwan University, Suwon 440-746, Republic of Korea
› Author Affiliations
Further Information

Publication History

Received: 27 March 2012

Accepted after revision: 14 May 2012

Publication Date:
26 June 2012 (online)


Abstract

Concise and efficient syntheses of d-lyxo-phytosphingosine and pachastrissamine were achieved utilizing a chiral oxazine. The key features in these strategies are the stereoselective intramolecular oxazine formation catalyzed by palladium(0), and intermolecular olefin cross-metathesis.

Supporting Information

Primary Data

 
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