Table 1.

Construction of the 1,2-Oxazadecaline Core of Trichodermamides from Benzoquinone and Ethyl Pyruvate Oximes 16a–d

Entry	Oxime	Base	Yield, %a
1	16a	LDA	–
2	16a	LHMDS	–
3	16a	LiTMP	–
4	16b	LiTMP	–
5	16c	LiTMP	92
6b	16c	LiTMP	34
7c	16c	LiTMP	88
8	16c	KHMDS	11
9	16c	LiHMDS	6
10	16d	LiTMP	<5

^aReaction conditions: oxime 16 (1 mmol), 17 (1 mmol), base (2 equiv.) THF (c = 0.16M), −78 °C.

^b1 equiv of LiTMP was used.

^cReaction was carried out on a 40.8 mmol (10 g of oxime 16c) scale.