Table 2. Preparation of Protected 1-Naphthyl-C-glycals 9a–b and 10.

entry	derivative	PG	E	conditions	product, yield (%)a
1	5a	MOP	BPin	A	9a, (86)
2	6a	MOP	SnBu3	B	9a, (76)
3	5b	EE	BPin	A	9b, (79)
4	6b	EE	SnBu3	B	9b, (93)
5	7	EE	BPin	A	10, (72)
6	8	EE	SnBu3	B	10, (87)
7	2b	EE	H	C	9b, (43)
8	2b	EE	H	D	9b, (20)

^aIsolated yield; reaction conditions: (A) Pd(PPh₃)₂Cl₂, 1,2-dimethoxyethane (DME), Na₂CO₃, 80 °C; (B) Pd(PPh₃)₄, toluene, 120 °C; (C) (1) t-BuLi, InCl₃, tetrahydrofuran (THF), (2) Pd(Ph₃P)₂Cl₂, reflux; (D) (1) t-BuLi, ZnCl₂, THF, (2) Pd(Ph₃P)₄.