Table 1. Reduction Studies of Δ⁹-THC (1) To Furnish HHCs 4a and 4b.

^aIsolated yields.

^bRatios determined from isolated material using ¹H NMR.

^cYields reflect the average of two isolation experiments.

^d38% yield of recovered 1, average from two isolation experiments.

^e20 mol % of Fe(acac)₂, 20 mol % of PhSH, and 4 equiv PhSiH₃ were initially added portionwise, followed by the second portion after 17 h.

^f10% yield of recovered 1, average from two isolation experiments.