Total synthesis of (+)-taberdicatine B and (+)-tabernabovine B

The first total synthesis of (+)-taberdicatine B and (+)-tabernabovine B has been accomplished in 10 steps with 26.9 % overall yield and 15 steps with 7.3 % overall yield, respectively. The prominent features of this efficient synthetic strategy include the following: (1) (+)-taberdicatine B and (+)-tabernabovine B were accessed from common advanced intermediates by varying the substituents; (2) a one-pot asymmetric bromocyclization/hydrolysis was explored to assemble HPI skeleton; (3) Dieckmann condensation to form β-keto ester for the assembly of seven-membered ring; (4) an ester reduction/amide semireduction/cyclization sequence was applied to form the cage-like framework. The first total syntheses of (+)-taberdicatine B and (+)-tabernabovine B have been accomplished. The prominent feature of this synthetic strategy is that (+)-taberdicatine B and (+)-tabernabovine B were accessed from common intermediates by varying the substituents, which could be applied to the synthesis of natural product analogues. [Display omitted]