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. Author manuscript; available in PMC: 2018 Apr 12.
Published in final edited form as: J Am Chem Soc. 2018 Feb 21;140(9):3394–3402. doi: 10.1021/jacs.7b13616

Table 4.

Optimization of heterodimerizationa and synthesis of (−)-calycanthidine.

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Entry graphic file with name nihms956192t3.jpg graphic file with name nihms956192t4.jpg solvent additive temp % yield dr (C2:meso)
1 H Me THF — rt 21 1:1
2 H Me THF — −40 ºC 10 2:1
3 Me H CH2Cl2 — rt 48 5:1
4 Me H CH2Cl2 — −40 ºC 30 14:1
5 Me H CH2Cl2 TFA (1 equiv) −40 ºC 71 14:1
Diastereoselective synthesis of (−)-calycanthidine
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a

Optimization reactions performed on a 0.025 mmol scale. Yields and diastereomeric ratios were determined by 1HNMR analysis of the crude reaction mixtures. Optimized heterodimerization reaction performed on 2 mmol scale.