161772-32-3Relevant academic research and scientific papers
Synthetic studies toward the microtubule-stabilizing agent laulimalide: Synthesis of the C15-C28 fragment
Messenger,Davidson, Bradley S.
, p. 801 - 803 (2007/10/03)
The C15-C28 fragment of the paclitaxel-like antimicrotubule agent laulimalide has been synthesized in 12 linear steps with an overall yield of 14%. The methyldihydropyran ring of the side chain was efficiently prepared using ring-clo
Total Synthesis of Halicholactone and Neohalicholactone
Critcher, Douglas J.,Connolly, Stephen,Wills, Martin
, p. 6638 - 6657 (2007/10/03)
The total synthesis of the marine natural products neohalicholactone (1) and halicholactone (2), in enantiomerically pure form, are reported. Key steps in the synthesis of each compound include a cis-selective Wittig reaction, stereoselective cyclopropanation, nine-membered lactone formation using the Yamaguchi method and late-stage stereoselective Cr(II)/Ni(II) mediated coupling of vinyl iodides 39 and 50 with aldehyde 14. In the case of the neohalicholactone synthesis the two major components which were coupled in this convergent synthesis were each derived from the enantiomers of commercially available malic acid. The synthesis served to confirm the original assignment of absolute configuration which was made by Yamada and Clardy. We also demonstrated, through the preparation of diastereoisomers, that another reported compound closely related to neohalicholactone is likely to be the C-15 epimer 67.
Synthesis and X-ray crystallographic structure of the right-hand hemisphere of halicholactone and neohalicholactone
Critcher,Connolly,Mahon,Wills
, p. 139 - 140 (2007/10/02)
The synthesis and X-ray crystallographic structure of the right-hand hemisphere of the marine natural products halicholactone and neohalicholactone, which contains a nine-membered lactone and cyclopropane ring, is reported.
