Stereoselective total synthesis of 4-((3S,5R)-3,5-dihydroxynonadecyl)phenol

• Published in: Tetrahedron letters Vol. 55; no. 8; pp. 1395 - 1397
• Main Authors: Yadav, J.S., Reddy, P. Adi Narayana, Kumar, A. Suman, Prasad, A.R., Reddy, B.V. Subba, Al Ghamdi, Ahmad Alkhazim
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 19.02.2014; Elsevier
• Subjects: 1,3-syn Reduction; Alkylation; Chains; Chemistry; Chemistry, Organic; Construction; Cross metathesis; Hydrogenation; Metathesis; Physical Sciences; Prins cyclization; Ring opening; Science & Technology; Synthesis (chemistry); Tetrahedrons; Cross metathesis; 1,3-syn Reduction; Prins cyclization; RING-CLOSING METATHESIS; REDUCTION; CURCUMIN; BETA-HYDROXYKETONES; SEQUENCE; ANTI-1,3-AMINOALCOHOLS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2013.12.056

A stereoselective total synthesis of 4-((3S,5R)-3,5-dihydroxynonadecyl)phenol has been accomplished in two different synthetic approaches. In the first approach, Prins cyclization has been successfully utilized to produce the anti-1,3-diol unit, which was further converted into a required syn-1,3-diol through Mitsunobu reaction. The side chain was constructed through cross metathesis and hydrogenation sequence. In the second approach, the chiral syn-1,3-diol was prepared by a sequence of reactions such as alkylation of 1,3-dithane with (R)-epichlorohydrin, ring opening of the epoxide with vinylmagnesium bromide, and 1,3-syn-reduction of the β-hydroxyketone with NaBH4 in the presence of diethylmethoxyborane.