Table 2.

Synthesis of pyridine‐based PSBH scaffolds.

					Step
	R	n	R1	R2	A (15)[b]	B (16)[e]	C (17)[f]
a	Boc2N	0	H	H	85 %	60 %	95 %
b	Boc2N	0	H	Me	–	69 %	94 %
c	Boc2N	0	H	CF3	–	77 %	54 %
d	Boc2N	0	Me	H	87 %	60 %	94 %
e	Boc2N	0	Ph	H	92 %	68 %	83 %
f	Boc2N	1	H	H	78 %[c]	41 %	65 %
g	Cl	1	H	H	73 %[d]	79 %	91 %

Reaction conditions: [a] Boc₂O (2.5 equiv), DMAP (0.1 equiv), THF, 70 °C. [b] R′‐BF₃K or R′‐B(MIDA) (1.5 equiv), Pd(dppf)Cl₂⋅CH₂Cl₂ (10 mol %), K₂CO₃ (3.0 equiv), THF/H₂O, 70 °C. [c] Allyltributyltin (1.1 equiv), Pd(PPh₃)₄ (10 mol %), KF (2 equiv), toluene, 110 °C. [d] i‐PrMgCl.LiCl (1.5 equiv), allyl bromide (1.2 equiv), THF, −15 °C to RT. [e] LDA (1.2 equiv), alkyl bromide (1.5 equiv), THF, −78 °C to RT. [f] Grubbs II (5 mol %), CH₂Cl₂, 40 °C. DMAP=4‐dimethylaminopyridine.