Sains Malaysiana 38(6)(2009): 869–872

A Study Towards the Total Synthesis of TAN1251B

(Kajian bagi Mensintesis TAN1251B Secara Menyeluruh)

Aznuzilawati Asari*

Department of Chemical Sciences, Faculty of Science and Technology

Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Malaysia

Christopher J. Hayes

School of Chemistry, University of Nottingham

University Park, Nottingham NG7 2RD, United Kingdom

Received: 18 February 2009 / Accepted: 20 April 2009

ABSTRACT

A synthetic route towards the synthesis of TAN1251B was developed utilizing an alkylidene carbene insertion reaction as a key step to construct the quartenary centre. The α-hydroxylation of the 5,6-spirocyclic enone with iodosobenzene was successful to give a mixture of diastereomer compounds 20 and 21 in 1:1.2 ratios.

Keywords: TAN1251B; alkylidene carbene; α-hydroxylation; iodosobenzene

ABSTRAK

Laluan sintetik bagi mensintesis sebatian TAN1251B dikembangkan dengan menggunakan tindak balas penyelitan alkilidin karbena sebagai langkah untuk menjana pusat kuarterner. Tindak balas penghidroksilan 5,6-spirosiklik enon dengan iodosobenzena telah berjaya memberikan campuran hasil diastereomer 20 dan 21 dalam nisbah 1:1.2.

Kata kunci: TAN1251B; alkiliden karbena; α-penghidroksilan; iodosobenzena

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*Corresponding author; e-mail: asnu@umt.edu.my