A Convergent Route to the Galbulimima Alkaloids (−)‐GB 13 and (+)‐GB 16

Total Synthesis of the Galbulimima Alkaloid (−)‐GB17

“…While early work focused on himbacine ( 1 ), most recent efforts have been directed at preparing the more complex members of the family. The first synthesis of GB13 ( 2 ) was reported by Mander and MacLachlan in 2003,6a with subsequent reports from the groups of Movassaghi, Chackalamannil, Evans, Sarpong, and Ma 6b–f. Himgaline ( 3 ) can be synthesized from GB13 ( 2 ), as shown by the groups of both Chackalamannil6c and Evans 6d.…”

Total Syntheses of (±)‐Spiroquinazoline, (−)‐Alantryphenone, (+)‐Lapatin A, and (−)‐Quinadoline B

“…The latter could be converted into 39 by refluxing in toluene 14. Finally, treatment of 39 with i Pr 2 NEt/KI to form the pyrrolidine ring15 afforded 9 (${\left[ \alpha \right]_{\rm{D}}^{20} = }$ −52.7 ( c =0.1, MeOH); lit 2e. ${\left[ \alpha \right]_{\rm{D}}^{20} = }$ −44.7 ( c =0.01, MeOH)).…”

Total Synthesis of (±)‐Merrilactone A

“…Et 2 O,6c or SnCl 4 6c resulted in lower yields (48–57 %) of 3 , the structure of which was confirmed by X‐ray crystallographic analysis (see the Supporting Information) 16. As mentioned above, the C ring could be formed through a reductive carbonyl–alkene coupling reaction 7c,d. Compound 3 was cyclized to give the desired tetracycle 2 (88 %) as essentially a single diastereoisomer (d.r.=20:1) by treatment with SmI 2 in THF.…”