Table 1.

Stereochemical control in enone reduction and introduction of the C12 stereogenic center

Entry	Conditions	Yielda	65:66 (trans:cis)
1	Li, NH3, THF, −40 °C	64%	1:2
2	Na, NH3, THF, −78 °C	85%	1:1
3	K, NH3, THF, −78 °C	82%	1:1
4	K, t-BuOH, NH3, THF, −78 °C	80%	1:3
5	Karstedt’s catb, Et3SiHc	92%	1:5
6	t-BuCu, DIBAL-H, HMPA, THF	86%	1:>20
7	H2, Pd/C, EtOAc	94%	6:1
8	H2, Rh/alumina, EtOAcd	93%	8:1
9	H2, Rh/C, EtOAcd	93%	15:1
10	H2, Pt/C, EtOAc	trace	nd
11	H2, Ru/C, EtOAc	trace	10:1

^aYield of purified material after column chromatography

^bKarstedt’s Pt hydrosilylation catalyst

^cfollowed by TBAF, THF to convert enoxysilane to ketone

^dfollowed by PCC, Celite, CH₂Cl₂ to reoxidize some carbinol.