Callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata
Callystatin A (1) has been isolated from the marine sponge Callyspongia truncata and the plane structure including parts of the absolute configurations elucidated. 1 exhibited potent cytotoxicity against KB cells.
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Synthesis of the tetrahydropyran fragment of (+)-Ratjadone A
2021, TetrahedronCitation Excerpt :The first total synthesis of ratjadone A was accomplished by Kalesse et al. using vinylogous Mukaiyama aldol reaction and ring opening of an epoxide to generate the tetrahydropyran unit 2 of ratjadone A [4a]. The confirmation of assignment of the stereochemistry was accomplished simultaneously also by Williams et al. [5,4b] The synthesis of Williams et al. was based on Julia olefination to form the C14–C15 bond of 1 by combining the THP and pyrone units. The synthesis by Kalesse’s group involved a Heck reaction of the THP fragment 2 and the vinyl iodide 3 (Fig. 1).
Chiral sulfur-containing imide auxiliaries in medicinal chemistry
2019, Imides: Medicinal, Agricultural, Synthetic Applications and Natural Products ChemistryCallyspongiamides A and B, sterol O-acyltransferase inhibitors, from the Indonesian marine sponge Callyspongia sp.
2018, Bioorganic and Medicinal Chemistry LettersA closer look on various synthetic routes to Callystatin A: a cytotoxic marine sponge polyketide
2017, Tetrahedron AsymmetryCitation Excerpt :Acid-catalyzed cleavage of the acetal and subsequent oxidation with MnO2 in CH2Cl2 and pyridine furnished Callystatin A (Scheme 19). In 2002, Enders et al. achieved a flexible and convergent asymmetric total synthesis of Callystatin A.29 The retrosynthetic approach (Scheme 20) is based on disconnections of the C6–C7 and C12–C13 double bonds, which can be built up by means of highly E-selective Wittig olefinations between allyltributylphosphorus ylides derived from the corresponding allylic bromides 88 and 32.9 Aldehyde 4 is accessible from keto ester 90, which can be prepared in an almost enantiopure form by biocatalytic enantioselective reduction of a 6-chloro-3,5-dioxohexanoate under conditions recently used by this group.30
Callyptide A, a new cytotoxic peptide from the Red Sea marine sponge Callyspongia species
2016, Natural Product Research