- Stereoselective total synthesis of clonostachydiol
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A simple and efficient stereoselective synthesis of clonostachydiol was achieved using ethyl (R)-3-hydroxybutanoate 5 and methyl (R)-2-hydroxypropanoate 12 as readily available starting materials. The key steps involved in the synthesis were MacMillan α-hydroxylation, Horner-Wadsworth-Emmons (HWE) olefination, a Grignard reaction, and Hoveyda-Grubbs IInd generation catalyzed ring closing metathesis (RCM).
- Ramulu, Udugu,Ramesh, Dasari,Rajaram, Singanaboina,Reddy, Sudina Purushotham,Venkatesham, Kunuru,Venkateswarlu, Yenamandra
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p. 117 - 123
(2012/06/15)
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- A stereoselective approach for the total synthesis of clonostachydiol
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A stereoselective synthesis of clonostachydiol is accomplished using readily available (±)-epichlorohydrin as a precursor. The synthesis involves direct and straightforward reactions such as Sharpless asymmetric epoxidation, iodination, stereoselective op
- Yadav,Swamy,Subba Reddy
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scheme or table
p. 2773 - 2776
(2009/04/16)
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- Bioactivity profiling using HPLC/microtiter-plate analysis: Application to a New Zealand marine alga-derived fungus, gliocladium sp.
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Using HPLC/microtiter-plate-based generation of activity profiles the extract of a marine alga-derived fungus, identified as Gliocladium sp., was shown to contain the known strongly cytotoxic metabolite 4-keto-clonostachydiol (1) and also clonostachydiol (2) as well as gliotide (3), a new cyclodepsipeptide containing several D-amino acids. The absolute configuration of 1 was elucidated by reduction to 2, and two further oxidized derivatives of clonostachydiol (5, 6) were prepared and evaluated for biological activity.
- Lang, Gerhard,Mitova, Maya I.,Ellis, Gill,Van Der Sar, Sonia,Phipps, Richard K.,Blunt, John W.,Cummings, Nicholas J.,Cole, Anthony L. J.,Munro, Murray H. G.
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p. 621 - 624
(2008/09/20)
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- The first synthesis and determination of absolute stereochemistry of clonostachydiol - Part II
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The first total synthesis of clonostachydiol has been achieved from two appropriately protected hydroxy acids that are derived from (D)-xylose and 1,2-O-isopropylidene (D)-glyceraldehyde.This synthesis has proved the absolute configuration of four stereoc
- Rao, A. V. Rama,Murthy, V. S.,Sharma, G. V. M.
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p. 143 - 146
(2007/10/02)
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