A simple and modular strategy for small molecule synthesis: iterative Suzuki-Miyaura coupling of B-protected haloboronic acid building blocks.

Part A I. General methods S1-S2 II. Synthesis of boronate esters (Table 1) S3-S6 III. Competition studies (Table 1) S7 IV. Synthesis of haloboronate esters (Scheme 1) S8-S13 V. Selective Suzuki-Miyaura coupling with haloboronate esters (Table 2) S14-S18 VI. Deprotection of boronate esters (Table 2) S19-S22 VII. Total synthesis of ratanhine (Scheme 3) S23-S39 Part B VIII. NMR spectra Part C IX. X-ray data for 8e (.cif file)