Abstract
The first synthesis of Luffarin I, sesterterpenolide isolated from sponge Luffariella geometrica, has been accomplished from commercially available sclareol. The key strategy involved in this synthesis is the diastereoselective reduction of an intermediate ketone. Luffarin I against human solid tumor cell lines showed antiproliferative activities (GI50) in the range 12–17 μM.
Highlights
During the last few years, there has been intensive research for new natural pharmacologically active compounds
Marine sponges have been the source of a large number of relevant sesterterpenes with biological activities, including anti-feedant [4,5,6], platelet-aggregation inhibition [7,8] and anti-inflammatory [9,10]
The resulting α,β-unsaturated acids 24a/24b were transformed into ketone 26 by hydrolysis of the acetoxy group and oxidation of the resulting alcohol (25a/25b) with Dess-Martin Periodinane (DMP) [25,26,27] at low temperature and subsequent esterification of the carboxylic group with TMSCHN2 (Scheme 4)
Summary
During the last few years, there has been intensive research for new natural pharmacologically active compounds. The chemistry of marine organisms and of sponges in particular has led to the. Marine sponges have been the source of a large number of relevant sesterterpenes with biological activities, including anti-feedant [4,5,6], platelet-aggregation inhibition [7,8] and anti-inflammatory [9,10]. The luffarins (A–N), 1–14, Figure 1, were isolated by Butler and Capon from an Australian marine sponge, Luffariella geometrica [11]. We report the first synthesis and biological evaluation of luffarin I. Another sesterterpenolide with luffarane skeleton, luffalactone, has been synthesized previously [12]
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