Total synthesis of the proposed structure of pestalotioprolide A

Marine natural products

“…421 Pestalotiopsis metabolite (6S,1 0 S,2 0 S)-hydroxypestalotin 422 has been synthesised 423 and the proposed structure of pestalotioprolide A 424 has been prepared via total synthesis, but a mismatch between the magnitudes of optical rotation data between the reported value for the natural product and the synthetic compound indicate that the stereochemistry of the natural product requires further examination. 425 A number of known natural products were reisolated from Phakellia fusca and exhibited a range of activities. Penicillenol A 1 , 414 a tetramic acid derivative, displayed anti-TB activity whilst expansols A-F 426,427 were potent COX-2 inhibitors and all but expansol D were also potent inhibitors of COX-1.…”

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

“…Finally, basic hydrolysis of the resultant ester using aqueous lithium hydroxide in tetrahydrofuran/methanol gave the desired α,β-unsaturated acid 124 in 91% yield. Two key segments comprising (S)-hept-6-en-2-ol 125 [167] and α,β-unsaturated acid 124, after several steps, gave pestalotioprolide A 126 (Scheme 23). [168] Recently, a wide range of 14-membered bioactive naturally occurring compounds were extracted from mangrove derived endophytic fungus Pestolotiopsis microspora by Liu and coworkers.…”

Total Synthesis of Pestalotioprolide E and Structural Revision of Pestalotioprolide F

“…Many of these members are reported to exhibit good to moderate in vitro anticancer activities . Attractive architectural features, good bioactivities, and natural scarcity made them promising targets for chemical synthesis . In continuation of our ongoing program on the synthesis of bioactive natural products, especially on the pestalotioprolide family of macrolides, we envisaged the total synthesis of pestalotioprolides E and F to get these materials in sufficient quantities to allow further biological studies.…”