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Synthesis 2011(19): 3180-3184  
DOI: 10.1055/s-0030-1260183
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Route to a Concise Stereoselective Synthesis of Cytotoxic (3S,5S)-1-(4-Hydroxyphenyl)-7-phenylheptane-3,5-diol and Its (3R,5S)-Isomer

S. Purushotham Reddy, K. Ashalatha, D. Kumar Reddy, B. Chinna Babu, Y. Venkateswarlu*
Organic Chemistry Division-I, Natural Products Laboratory, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: luchem@iict.res.in;
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Publication History

Received 31 May 2011
Publication Date:
24 August 2011 (online)

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Abstract

Maruoka asymmetric allylation using bis[(R)-2,2′-binaphthoxy)(isopropoxy)titanium] oxide, and Jacobsen’s hydrolytic kinetic resolution (HKR) using (R,R)-salen-Co(OAc) catalyst were used as key steps for the construction of syn- and anti-1,3-diol systems in the synthesis of cytotoxic (3S,5S)-1-(4-hydroxyphenyl)-7-phenylheptane-3,5-diol and its (3R,5S)-isomer.

Key words

diarylheptanoids - cytotoxic - Maruoka asymmetric allylation - Jacobsen’s hydrolytic kinetic resolution

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