PMID- 28346788
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20180613
LR  - 20180613
IS  - 1523-7052 (Electronic)
IS  - 1523-7052 (Linking)
VI  - 19
IP  - 7
DP  - 2017 Apr 7
TI  - Three-Step Catalytic Asymmetric Total Syntheses of 
      13-Methyltetrahydroprotoberberine Alkaloids.
PG  - 1594-1597
LID - 10.1021/acs.orglett.7b00414 [doi]
AB  - (S,R)-N-PINAP was identified to be the chiral ligand for highly enantioselective 
      CuI-catalyzed reaction of tetrahydroisoquinolines (THIQs), alkynes, and 
      2-bromobenzaldehyde derivatives. This enables us to accomplish the first 
      asymmetric total synthesis of 12 natural 13-methyltetrahydroprotoberberine 
      (13-MeTHPB) alkaloids in only three catalytic steps with 47-64% overall yields. 
      In addition, the Pd-catalyzed reductive Heck cyclization was successfully 
      extended to three Pd-catalyzed domino reactions (Heck/Suzuki, Heck/Sonogashira, 
      and Heck/Heck), which greatly expands the synthetic utility of this catalytic 
      strategy and allows expeditious access to 13-substituted 
      tetrahydroprotoberberines for further bioactivity evaluation.
FAU - Zhou, Shiqiang
AU  - Zhou S
AD  - Department of Chemistry, The Hong Kong University of Science and Technology , 
      Clearwater Bay, Kowloon, Hong Kong, China.
FAU - Tong, Rongbiao
AU  - Tong R
AUID- ORCID: 0000-0002-2740-5222
AD  - Department of Chemistry, The Hong Kong University of Science and Technology , 
      Clearwater Bay, Kowloon, Hong Kong, China.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20170327
PL  - United States
TA  - Org Lett
JT  - Organic letters
JID - 100890393
EDAT- 2017/03/28 06:00
MHDA- 2017/03/28 06:01
CRDT- 2017/03/28 06:00
PHST- 2017/03/28 06:00 [pubmed]
PHST- 2017/03/28 06:01 [medline]
PHST- 2017/03/28 06:00 [entrez]
AID - 10.1021/acs.orglett.7b00414 [doi]
PST - ppublish
SO  - Org Lett. 2017 Apr 7;19(7):1594-1597. doi: 10.1021/acs.orglett.7b00414. Epub 2017 
      Mar 27.