Total synthesis of Aplyronines A, B, C (partial):
| Reference: | Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakakura, A.; Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5326. DOI |
| Reactions: | O-H → O-C(O)R • O-Bn → O-H • Alkyl-OH → Aldehyde-α-OR • Alkyl-SO2R → Alkyl-H • Li-Sulfone+Alkyl-X • Alkyl-X+Li-R • Julia-Lythgoe • Julia-Lythgoe • Cu-Me+Aldehyde • |
| Reagents: | LiCHR-Sulfonyl • LiCHR-Sulfonyl • Acetic anhydride, DMAP • Na(Hg) • LiCHR-Sulfonyl • HMPA (solvent) • H2, Pd • Dess-Martin • Me-Cuprate • Dess-Martin • LiCHR-Sulfonyl • Na(Hg) • Na(Hg) • HMPA (solvent) • |