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. 2016 Jul 8;21(7):892. doi: 10.3390/molecules21070892

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© 2016 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).

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Scheme 16 — Synthesis of hapalosin (80) and derivatives. Reagents and conditions: (a) (1) Bu₂BOTf, Et₃N/CH₂Cl₂, then Me(CH₂)₆CHO; (2) n-BuLi, BnOH/THF; (3) Ref. [193]; (4) NaOH, DCC, DMAP/CH₂Cl₂; (5) H₂, Pd(OH)₂/EtOH, vinyl-2-hydroxy-3-methylbutanoate, DCC, DMAP/CH₂Cl₂; (6) TFA/CH₂Cl₂, DPPA, i-Pr₂NEt/DMF; (b) (1) i. DCC, DMAP/CH₂Cl₂, ii. H₂, Pd(OH)₂/EtOH, (2) DCC, DMAP/CH₂Cl₂; (3) i. HF-pyridine, ii. (Ph₃P)₄Pd, morpholine, then TFA, iii. DPPA, EtNt-Pr.